Another consideration is if it really makes sense for him from an investment stand point.

In my state, property taxes can be low due to Homestead tax exemptions on primary residence, especially if the owner has lived there a considerable time, because there's a cap on tax increases each year for homesteads.It's always a good idea for agents to forewarn buyers not to rely on property tax estimates long before closing.

Provide them over-the-top paperwork on your projects...with many diagrams, extensive product info, contractor drawings, warranty info.

I would start looking at areas where you could maintain that day job and then compare the price/rent ratios in those areas as well as take into consideration the potential for appreciation.

Definitely taking it into consideration. 

@Devon Spooner Another consideration not mentioned is what the area is like.

I'm curious how some of the experienced investors would structure a lease to purchase deal, from the seller's perspective.What types of things should be taken into consideration when selecting the rent/mo?  

There were a lot of houses I would go to and see fresh snow with no foot prints that meant no one had been to the house and that was a consideration in the offer I made.Looking forward to snow this year :)

cite=82.45If the property is owned free and clear and there is no consideration given then you can document the affidavit as a gift, making it a taxable event for you personally and not the Seller. 

You have no idea...It really isn't hard, though, to draw a distinction between commercial signs that might be up for months, and political signs that are not only up for less time, but are exactly the sort of thing the First Amendment is meant to protect.