The rental property is in a HOA community that has a 30 day minimum lease term so converting to a STR isn't an option. 

Either option should be easy with your income level.

I figured I will meet up with different PMCs during our (typical) 2 year stay in the different towns.

If you’re working with a lower budget, say $100-$150k, Cleveland could be a fantastic option.

Here are a few options you might consider:Home Equity Loan or HELOC: If you own another property with sufficient equity, you might be able to take out a home equity loan or a home equity line of credit (HELOC) to cover the $140K.

-Make sure the contract states:-what you are doing for the "sweat equity"-Options for parties on both selling, equity, refinancing, etc.

In a case like this often the brokerage/agents get a cut of that EMD that you would typically forfeit.

However if you only invest it in training, then at the end you have lost $50,000 and still don't own anything.There are a lot less inexpensive ways to learn about real estate in my opinion.Don't fall for any high pressure techniques from any guru.....the typical scenario is to go to a free 2-3 hour training session. 

I'm wondering, do you typically engage an attorney early on to assess the situation and what will be needed?

I've raised and torn down single family homes, gutted condos, and five and six story buildings.I can tell you that owning the land and the building allows you to have options.