@Ariel Vincent You're so right.I definitely want to be able to assume the risk, and I would LOVE live on the property (it's beautiful and it's going to KILL on AirBnb if I can get her to agree to this) but right now I just don't have the cash to lease in the traditional way. 

I attended college in that region. the beauty of it is that you can rent it out and have it cover the mortgage when YOU want, then you can enjoy it when you want to get away.

Here's the situation:I have a once beautiful 1970s house in a great neighborhood in a beach area (Lewes, DE).

I have been married just under 4 years and my wife and I have a beautiful little girl. 

People looking for a historic home are looking for character and having special items like 'these windows came from a school house' and the lighting came from there and these are the original fireplace mantels, that were completely stripped down to this beautiful tiger oak' makes a huge difference. 

This town is very high end, with an average sales price for SFRs at $750,000.To make it even more complicated, there are multiple barns and an outbuilding that's beautifully finished, with a gym and sauna. 

It's a beauty.  

You will find a ton of beautifully remodeled homes on the inside in neighborhoods that don't look that great, and finally, 3/2s rent a million times faster than 2/2 as it is a family area.

Depending on your area can be difficult but if you find the right deal and seller financing it's a beautiful thing. 

By that time, the only differences will be that the truck will be older, have aesthetic/mechanical issues, be worth a lot less, and nobody will be excited by how it looks or drives.