I'm not a fan of mega back door roth contributions, unless potentially if you're in the 22% tax bracket or lower.

I have them tell me how long a project will take to complete, and then I add buffer days or maybe up to 2 weeks, depending on how long / complex of a project it is and potentially accounting for weather if it is outside work.

Typically, I run a current income/expense column next to a ProForma column to show potential value add opporunties.I agree with @Robert. 

Once you go with a minimum 6 month lease your turnover costs, potential damage, make ready costs, repainting and repair costs, all go down dramatically.  

I am potentially looking into getting a trailer at the begining of the year getting a trailer that may need some work to rent out.

Younger buyers are still eager to enter the market, and as the economy shifts, there is potential for conditions to become more favorable.

Also when you are under contract and get condo docs, make sure to read the meeting minutes (for the past year if available) they will indicate if there are any talks of an upcoming special assessment (which you don't want).

I have not started, completed or participated in a syndication so tough to assess an ROI at this time.

You can still find positive cash flow (aka the 1% rule) and amazing appreciation potential.

These areas often have 3/2 SFHs in your range, with decent BRRRR potential.