The transfer fees/taxes for the deed can get into the $400 - $500 range for each of these. 

Getting started I wouldn't avoid single family homes, there are more of them, they cost less comparatively, and as Greg stated they are just less complex.

You should avoid flips if you're starting out.

Plus the added tax benefits to support my current situation ($120k a year as a "single" person with "0" dependents Uncle Sam definitely gets his cut) A home my family and I could use in the off seasons on vacation plus creating a unique experience with lifelong memories for our guests sounds great to me, regardless of whether it cash flows.

So my conundrum is do i just keep renting to a new tenant and deal with the maintenance expenses as they pop up, or do i try to get out now before a major expense pops up and just take the little bit of profit (less the capital gains tax)?

With property tax adjustments and the mortgage company requesting an additional amount for possible future increases.

This avoids the seasoning period and still allows conventional financing for the best rates. 

And if you ever come across a John Aaron in Florida, avoid him at all costs. 

I would include - try to avoid exceeding $250,000 a year in reported income to avoid the Obamacare tax increase through smart planning of your sales of capital investments.  

I am just wondering what should I be doing next as far as taxes, savings, investing, and reading.