My heart is leaning OC given the family tie, obvious synergies with travel, etc. but my mind is leaning Tampa given the hard numbers. 

Devil's Advocate:  If I put 20% of my money down, I struggle with the concept of positive cash flow as my down payment is now tied up and is NOT being taken into consideration for the "cash flow positive" scenario.  

If so, there are ways to get the court to release the home or at least tie it up until the probate is finished.

Here’s the problem my money is tied up in another property out of state.

Making the purchase all cash, is not as awesome as it seems – we tied up $195,000, which made things a little tough specially because we finalized another purchase right after this one.Things we learned: (1) having cash on hand is useful, we saved ourselves some money by financing the project ourselves.

I agree with you that cutting every cost in half and saying "that half's for the house" is completely bogus. 

I’m going for electrician, but I’m obviously not cut out for it and don’t want to waste my money or time since I pay for my own schooling and have little time for real estateIf I were to drop out I would have time to find a mentor, read, attend seminars, attend open houses, analyze more properties etc... my goal is to retire by 30 and I would be going to community college for another 3-6 years at the rate I’m going now.

It was built in 1917 and was done nicely I'm just not sure if corners were cut and that is hard to get down to until the inspection.Thanks in advanced for all your responses,MarieChele

Establish an area management company and tie yourself into that board of members and part owner.  

Then I used a company to create a Checkbook Control IRA LLC which allows me to pay the contractors directly instead of using the IRA custodian to cut checks.