Bryan,I am not qualified as an expert here but my understanding is that when you are exceeding the $14,000 limit during pre-full retirement years you are paying back SS benefits so as to boost future benefits.

This seems like a very good way to boost my Roth savings, as the contribution amount can be pretty large.* If it doesn't complicate things too much, I would also like to make a yearly (after-tax) Traditional IRA contribution, and roll that into a Roth IRA

The LLC, or other forms of checkbook control such as a Solo 401k or IRA Trust would dramatically reduce both per-transaction fees and more importantly all of the bureaucratic paperwork and delay that goes with a 3rd party custodian/transaction processor.  

Just like a junker prop can tank the value of the house next door, an updated and well-kept prop can help boost it's neighbors' numbers. 

And it is possible that it won't ever turn around ...Finally, the AV is far away from you (OP) ... unless you are looking to move out there to house hack, the distance will dramatically effect your ability to manage and control your investments.

By opening your search up across the country you dramatically increase the talent pool.

To do so would be in effect making undocumented contributions to the plan and artificially boosting the tax-sheltering value of the plan.Think of yourself as a fund manager putting someone else's money to work (your future self).

Just the answer to that question will result in dramatically different answers to your questions.  

Vacancy is 2% in Richmond and rents are increasing dramatically all over the Bay.

Even being $50 over market rate, I see a dramatic drop in tenant quality.