If you sell your only overachiever to go with a more leveraged position, you could have 2-3 properties that may cover themselves or even provide a little profit, but when the rental markets shift (and they do), now you have 2-3 properties that all require you to supplement for their shortages. 

Is simple forget all you know, go to local Investor Meeting meet investor flippers and wholesaler. 

Quote from @Dyllon Gibbs: Hi All,Does anyone have experience with rent guarantee insurance and any specific companies?

I have went down the path with 3 different banks and they all said the same thing.

All that being said, it might not be worth the cost of putting in parking, just be aware on the front end that you’re reducing your end buyer/rental pool by not having it. 

Hi all, My relative wants to combine their $500K personal exemption & a 1031 exchange to liquidate their rental properties without paying taxes, but they are worried about missing the180-day time limits for the 1031 exchange, so they want to involve their son-in-law (SIL).

Sights are set on all types of REI, but this will be a great start for us.I have been in the mortgage business for over 20 years.

Not that I am aware of, but I am not aware of all softwares on the market. 

I'm open to all suggestions and ideas!

In almost all cases when investors first come to us we say utilize the conventional route as much as you can.