If you aren't paying attention to your rental comps, your property will sit. 

She's been renting it for $2,800/month and the condo has a $600 monthly HOA.I want to offer her $350,000 for the condo (its a fair price for it), 5% down payment ($17,500) and pay her monthly $2,000 for 3 years, after which I would refinance and pay her out.

We have a 480k mortgage on it, we have a 400k heloc as well that I use for investment purchases and then refinance after we fix up to pay the heloc off.

I have the capacity to take on an additional $200K in debt on top of utilizing my HELOC, so long as when I am paying it down the monthly charges also go down.

Ideally I would try to get a 3/4 unit property somewhere in DC proper, PG County or Montgomery County (Takoma Park/Silver Spring), live in one unit and rent out the others. 

Pay penalties and interest if state comes back. 

Hi I recently had a tenant pay a full year rent upfront.

You lose the rent money that he didn't pay and you have to pay someone else to finish the job.

Most people in the forums are recommending Proper Insurance for STR insurance, and I was able to get a quote from them quickly.

You pay the minimum on your student loans and put anything extra into investments.