Wow, great thread. Here's my thoughts:
You're almost exactly where I was 10 years ago.... the numbers on those 2 SFRs.... except interest rates are lower.... so I was sitting at level/negative cashflow till I refinanced last year, at which point I have a positive $200/month (and pulled out cash to put into a 4plex, but that's a different thread).
Did I need a nice place to live in a good neighborhood? Yes. Do I regret buying it? No. Should I have done something different based on what I know now? Yes. Things I've learned since investing for several years: Don't be slow to make a low offer.... make an offer where the numbers make sense.... as far as the market is concerned.... you buy now, you'll only loose money if you sell it during a slump, so plan to hold it forever as one of your exit strategies that will mitigate any market downturn. HOA is as bad as PMI, I would have bought a house without if I were to do it again (don't know if this is an option where you are).
As far as avoiding PMI? I think if I were to Owner occupy a place, I would take advantage of the financing, and get 97% financed... then you are out 6k, and have 35k start on your next investment.....Sure you'll be throwing away a couple hundred/month, but you have more flexibility moving forward, and if you wait a year and some other units in the complex go for 250k, you should have comps to prove a new appraisal... and drop the PMI.
Last thought.... which may not apply to your location.... are there any multi's? I made a lot more progress once I moved into a duplex, and I've never looked back. Even now, I'm in a 2400sqft upstairs unit, and the whole mortgage is paid by the downstairs unit. Until next week when I pull out enough equity to leverage another 4-plex...
Always buy.... and always be careful