I have the opportunity to buy some real estate property thru a buddy of mine, title in hand but she hasn't paid property taxes in the past 5 years.

I've seen hand sketched site plans approved but these calculations are much more involved. 

But on the other hand there are homes that was listed on the MLS but never got sold and then went into foreclosures.

He did mention briefly there is a local airbnb management company here https://www.hosteaz.com that lets the owner be completely hands free from the airbnb.

I realize this is a little bit older thread, but I wanted to offer a hand with your wholesaling.

Life insurance companies on the other hand have longer term liabilities and they look for longer term assets (25-30 year loans) to match that.

On the other hand, York PA where I work is on the other side of the spectrum where the majority of houses are under 100K and there are two small colleges in the town (Penn state York, and York College).

I go to many in the Central PA, and sure there may be many newer investors, but there are also many seasoned investors/flippers who would be happy to lend a helping hand. 

On the other hand, if you feel confident in finding another home that will cash flow over $300/month then that is great as well.

Biggerpockets is usually my first stop to see if anyone has first hand experience with what I am doing.