The privacy, off grid, natural setting near JT seems to be very popular right now for short term rental.

I learn best when I jump into situations and problem solve when issues arise, but I don't feel like I've made any tragic mistakes or have overstepped my bounds to this point.

And then you get to the issue of actually needing to file a claim (in the dozen or so flips (not including rents) I have had 3 title issues arise post close).  

Account Closed I have read many of the books on real estate investing from the most popular writers. 

It is hard to come by triplexes that make sense numbers wise because it is such a popular product, lots of offers when any of the mutli-unit properties are available.Sounds like a well thought out approach, Jacksonville is a great area, good luck with your purchase!!

A GC will also generally take over fixing any subs mistakes that arise after the fact.Hiring subs yourself can save you a lot of money, but if your tile work is shoddy and the painter can't do their job because of it, you could have a hard time getting the tiler back on site.  

The reason I am looking in this area is because it has great schools and a rising population.

The second model and most popular on BP is buy in smaller markets where entry points are low (typically working class neighborhoods), put 20% - 25% down payment and push for monthly cash flow.

Cleveland, Ohio is the one I am most familiar with and it's also very popular with investors across the USA so I figured you'd get some value out of reading The Ultimate Guide to Grading Cleveland Neighborhoods.

You will need money for any initial repairs to each unit plus enough reserves for any future issues that arise.