However, the entire market depends on Robins Air Force Base, with not much else moving the needle.

For bookkeeping it depends on your portfolio.A portfolio of 1-3 SFR's can likely be a DIY project.For 4+ you may want to consider outsourcing.For tax prep, you'll likely want to have a pro handle it regardless of the portfolio size.

You are bleeding money now, but each year it might actually get worse depending on the financials. 

Depending on how long it takes you to save up the amount, you might want to also allow for inflation on that amount for your continued savings.[2]   Read Rich Dad poor dad.[3]   Think about getting a second job - possibly a temporary job - save a 100% of the money.Just my 2 cents.

It will depend on your preferences and how well you think you will tolerate having a room mate as you approach a new life with your partner.

I would still do due diligence such as whole property inspection, lead inspection (depending on when the property was built), appraisal, etc. 

It depends on your financial strength, the quality of the property, how many properties you own, etc.I like to start with one significant expense and three months of vacancy.

As for your ques if to wait, well, it depends on the market, in some parts of the country prices are still going up, slower, but still going up, other parts the prices are coming down, you know that area, what is happening there? 

I think you can go as high as 15% but it's cutting into your margins and depends if you are a GC yourself or not. 150k is close to a million or more.

I think this depends on your risk tolerance and your interest rate.