That would give you another exit strategy should you have to relocate for some reason.As for whether now is a good time to buy given that we may be at the top of the market - it is impossible to predict the markets.

Cash flow properties may be harder to find in Howard County (although certainly not impossible), but just crossing over into SW or Western Baltimore County you should find good opportunities for investing and still make your commute to NG doable until you are financially free.

Looks like it is peak market and it seems I could get the most its been worth in over 10 years.Options: Option1: Sell and take profits, reinvest into a newer house, nicer neighborhood and better cash-flowing property. 1031 is impossible to time so I would just take the tax hit.Option 2: Keep and continue getting 25% ROI/$300/mo cashflow on 12k total investment.It's not a slam dunk as a buy and hold, but its adding to my overall annual cashflow. when its paid off in 25 years, it will throw off $700-$800/month in cashflow so it will support retirement at 58-62.

I realize it's almost impossible to complete 12 years of schooling sitting in front of teachers who all belong to the same union and not believe this idea.

I  know it is impossible to predict the future but so long as it is generating positive cash flow would you keep it?

Finding the "right market" is nearly impossible, it's more about picking a market that works.

So far I’ve been managing my long term tenants but I’m moving to have more short term rentals and managing that with my job would be close to impossible.

When I started as an agent it was near impossible for me to obtain a loan without a track record of income. 

However, no matter what anyone says it is impossible to align the interests of the sponsor and the investor. 

It's not impossible, but it's not easy either.