You own a parcel of land (the "Property") and have decided to sell it to someone (the "Purchaser") on the understanding that the Purchaser uses the Property for a specified purpose and develops the Property with particular/particular types of improvements. A more or less common example of this situation is where the current owner (you) subdivides a Property into a number of building lots and then enters into purchase and sale contracts with a number of buyers who promise that they will use their lots solely for, say, recreational purposes, and additionally promise you that they will, within a specified period of time, build cottages on the lots, with the cottages having to be constructed to meet, to a greater or lesser degree, your specifications. Such an arrangement may be encouraged or indeed required by the municipal/local government for the jurisdiction in which the Property is situated.
You know that you can enforce the Purchaser's promises by court action brought against the Purchaser, but you also know that positive - as opposed to negative - covenants (promises) are not considered interests in land which are capable of being enforced against a successor in title to the original contracting Purchaser, absent the original Purchaser's successor undertaking to you directly to be bound by the original Purchaser's promises to you. Instead, you accept the suggestion of a lawyer, who has a little, but not sufficient knowledge of these matters, to include an option in your favour to buy back the Property from the Purchaser, if and when the Purchaser breaches its promises to you. The lawyer tells you that such an option is an interest in land and thus, if properly recorded (caveated) against the title to the Property, will indeed bind all successive title holders of the Property.
The use of options to purchase in this situation is fairly common, and while it is true that a "pure"/"unadulterated" option to purchase does constitute an immediate interest in land, an option in the above-described situation - which is really a conditional option which will only arise in the future upon the occurrence of some event which may or may not happen (ie., the original Purchaser's breach of its promise(s) to you) - is not an interest in land. The arrangement is binding between the immediate parties to it, but will not "follow" the title into the hands of subsequent owners, barring an undertaking by a subsequent owner to be bound by the arrangement (ie., the conditional option). The case law makes it clear that this type of a (conditional) option is really akin to a first right of refusal (which is also not an interest in land, although some people think it is and even try to caveat it), because unless and until the Purchaser breaches its promises to the promisee, the promisee has no unequivocally existing right to compel (at its choice) reconveyance of the Property.
Can an original land owner enter into any sort of arrangement with its Purchaser which would enable the original owner to get the Property back where the Purchaser's promise(s) is/are breached by a successor in title, with the original owner being able to enforce the promise(s) against a successor in title? The answer is "yes", although counsel for the original owner will have to be very careful how he or she drafts the contract.
Before dealing with the law pertaining to this matter, please keep in mind that there are two elements of the Purchaser's promise(s) referred to above, namely:
(i) the promise to only use the Property for a specified purpose; and
(ii) the promise to develop/construct specified improvements on the Property.
Common law recognizes two similar, but in fact, in terms of legal consequences, substantially different, types of fee simple estates in land, namely:
(i) a determinable fee simple. This is a grant of fee simple ownership by the original owner to the transferee to last and exist during a period of time in which, or only for so long as, the transferee uses the Property for a specified use or uses. Upon the Property ceasing to be used for the specified purpose or purposes, the fee simple ownership of the Property automatically reverts to the original owner, that is, reversion occurs without any exercise of discretion, an option, etc. on the part of the original owner. The determinable fee simple is an interest in land and as such is caveatable against the title to the subject Property and will bind successors in title.
(ii) a fee simple which is terminable upon a condition subsequent. Here, where the Purchaser breaches its promise(s) to the original owner, then the original owner has a right or choice to require forfeiture of the Property back to the original owner. Such an arrangement is enforceable between the parties but is not an interest in land which would bind successors in title.
Case law and legal commentators have made it clear that "the law has been jealous in its scrutiny of conditions subsequent and will readily hold them void as offending pubic policy, as incapable of performance, or for uncertainty". In such a case, when the Court holds the condition subsequent to be void, the result is that the fee simple estate becomes absolute in the hands of the (then current) owner. On the other hand, in the case of a determinable fee simple where the Court holds that the requirement specified to end the estate is void, typically due to uncertainty, the transferred estate will be held to have terminated, with the result that ownership will automatically revert to the original owner (ie., the result would be the same as where the terminating requirement was held to be valid and enforceable and that such event had occurred).
So, going back to the original example, if you are contemplating the sale of your Property, and you wish to induce performance of the purchaser's use/development promise(s) to you with the threat of forcing the return of the Property to you, and you would in fact want the Property back in your hands if the Purchaser (or its successor in title) ceased to use it in accordance with the Purchaser's promise(s) to you, how should the contract be worded?
The key is to word the agreement/transfer of ownership so that the conveyance is to be "for so long as" or "during when" the conveyed lands are used for one or more specified purposes only, or possibly "for so long as" or "during when" the lands are used in accordance with certain specified (typically, development) requirements. The writer uses the word "possibly" here because when you move from characterizing the transferred ownership as being required to be utilized for a specified use or uses, to specifying compliance with requirements other than "purely" usage obligations, you start to get into the area of what may be, in any particular instance, requirements which obligate the owner to take specific actions and/or expend monies in order to meet the requirements. The Courts have traditionally frowned on promises binding successors in title whereby the owner is obliged to take certain actions and/or expend monies. In other words, it is one thing to require that the land be used only for "recreational purposes", but perhaps quite another to require that the owner (and its successors in title) build a cottage (in accordance with certain specifications) by a certain deadline. The latter requirement, which would obligate the owner (or its successor) to take certain actions and/or expend funds, are requirements which are substantially akin to the imposition of positive - as opposed to (passive) negative - covenants/promises on or against land, and as such, may not be enforceable against successors in title.
Nevertheless, the dividing line between a grant of ownership "for so long as"/"during when" the land is used only for specific purposes, and a grant of ownership "for so long as"/"during when" the land is used in accordance with specific (development type) requirements, is a fine one. Thus, counsel would no doubt be better advised to at least attempt to arrange for a conveyance of ownership "for so long as"/"during when" the land is utilized in accordance with specific development type requirements, than attempt to establish an arrangement whereby the vendor has a conditional option to re-acquire the land where the Purchaser (or its successor) breaches the obligation to develop the Property in accordance with specified development type requirements.
Land owners contemplating the imposition of usage/specific development type requirements on one or more purchasers from them by way of the establishment of determinable fee simple arrangement(s), should take into account the likely reaction of a Purchaser's (or its succesors') mortgage financier(s). No mortgage lender would want its security to suddenly disappear by virtue of reversion of ownership of the mortgaged land back to the mortgagee's mortgagor's vendor, free and clear of the lender's security. At the very least, a mortgagee would want its mortgage security to "follow" ownership of the Property back to the vendor, with some assurance that the vendor would be bound - at least on a non-recourse basis - under the mortgagee's security. Whether the original owner/vendor would be willing to be bound by a Purchaser's mortgage financing may be a difficult question to answer, but it is certain that no mortgagee in its right mind would advance money to a mortgagor where the mortgagor's ownership could suddenly disappear through no fault of the mortgagee.