I have been on all sides of construction, so that part is where I am most knowledgeable.The appeal of cash flowing from a rental is nice.

Once an offer is signed in massachusetts by both parties it is considered an enforceable contract.This serves as better proof the seller actually was delivered the offer and read through it.

Contract is not bidding until both parties sign AND IT IS DELIVERED!

Heck, you're not even a party to the lease option agreement between the seller and the buyer after you assign, unless you structure a sandwich lease option instead of assigning).

If landlording has become a chore for them they might be willing to do a deal with you that is favorable for all parties.

This is not the same process as a SFR purchase, where the buyer obtains a letter of qualification from a dubious mortgage broker; this is a very intensive evaluation.That being said, nothing is to stop any interested party, qualified or not from making an unsolicited offer.  

If you own the land outright you will be able to negotiate with parties your interested with working with.

@Eric Hansen However, a big part is how do your fiance feel about real estate investing?

How would you work it to make it fair for both parties?

Of course the IRA part is always TBD, but anybody using NCH For business account administration?