I see that it would be a huge project, and also know it would be my first...However, I just can't help but see the huge potential upside and I don't want it to be clouding what it really is. 

Any bookkeeper who isn’t using cloud bookkeeping isn’t going to be keeping up with the pace of changes in real estate.

@Eric Brantley There could be a silver lining in this cloud.

Chase rent?

Investors are successful in every part of the metro area, as well as Duluth, Rochester, St Cloud, etc.

So I am debating using Quickbooks  or something cloud based and a little simpler. 

Then the transaction from B to C (you) is a totally separate transaction with title insurance.Before you close the title company taking care of the transaction / or the attorney as they use both in St Louis will provide you with a preliminary title showing all the problems they can find with title - the middle buyer is not going to be able to close with clouded title unless their contract says that they will buy with title defects, in which case if they are assigning the contract to you, would have you taking over their original contract.In a double close however there are usually 2 separate contracts and you need to read the one you are a party to so you can see what you agreed to in regards to marketable title.

I've had it.I'm ready to do something crazy and different....I need to do something before it's really too late and I get too old to chase dreams.I think I know what I want but my mind is clouded by stress and I can't see it all clearly yet.  

We used that 100 K and bought a block triplex in Saint Cloud with pool a year ago also in central Florida for $425,000 at a 2.8 percent interest rate.  

I currently use Tenant Cloud for managing cash flow and tracking accounting.