I'm not smart enough to work out the math of which option would be best, or how long it would take for the syndication option to overtake the DST option. 

Or if the tracking my route $20 option was included already with the monthly rate, that would be awesome.

The other option is hard money, how good of an idea is using hard money for my first deal?

Start there it will offer many more options and choices than the 'loan officer' at your bank branch.

Purchase was $188k and has been depreciated for 12 years to date.The online Capital Gains calculators show an outright sale losing over 30% to capital gains, depreciation recapture and the 3.8% Medicare tax (an extra stick in the eye).

Pricing and rates change constantly so if you are seeking cash out of a rental property you can entertain a second DSCR equity loan up to 70CLTV to keep your first in place or take a look at a full new cash-out option.

@Stephanie Gledhill The credit union you found looks like a great option.

While this can be risky and might come with penalties or taxes, it can be a viable option if managed wisely.

Based on budgeting, section 8 seems like a viable option without any major cons.

For the rehab loan, I would look at options longer than a 12-month loan.