I have a subject to deal that has a home owners association.

Is it subjective or should it be objective?

Brent the reason I brought that up is that there's different ways of taking title and there's different kinds of title, strongest title subject to where you actually get a warranty deedThe land contract in Ohio is a great tool to buy on  terms.

Does it make sense to purchase a rent-ready property subject-to for the amount a seller is behind on payments (and use that purchase payment to bring the seller's mortgage current), give the seller a, let's say, 5-year option to purchase, and rent the property out to someone else for a few years up to 5 years when the original seller is ready to buy back the title?

Evictions and turnover do happen more frequently due to tenant selection pool.    

The banks usually take their sweet time and the listing agent is subject to their whims just as you are.

Liens are not enrolled until a tax debt is no longer subject to appeal or the time to appeal is exhausted.

Do you live close enough to drive by or visit the house frequently to make sure of its continued condition?

If you have the property under contract and you still want to buy it you can file a kid pendens notifying any potential buyers the property is subject to dispute.This could force the hand of seller to continue on with a sale to you.

I would fine deals you really want to do and make them subject to you obtaining finance simple.