Newbie from Boston area!

[Craig W.]

New to the site and want to say hello to everyone. 

My name is Craig and I’m in the commercial construction field in the Boston area. I have been dabbling in real estate as a side passion for the last 10 years with ok success. Life is a little more complicated now with a wife and child to contend with. I would like to continue investing in a safe way and be able to setup myself and family up for the long run. 

I started when I was 24 buying a bank owned right in the down turn. I completely renovated it and was able to turn for a profit 2 years later. In between then and now I did 2 condo flips and another single family fixer up I lived in and sold. 

Fast forward to now, my wife and I bought 1.5yr ago in a rising market. Purchase was 355k for a 2/1 1200sf .3 acre single family fixer up 25min from downtown Boston. We have put approximately 50k into it including new kitchen, new bath, new windows, new paint, new lighting, plumbing work, new deck, moved driveway to side street. (Lot could have potential for subdivide/condos?) 

At this point we are ready to move on from living here. We just had our first child and find the road to be too fast and the house to be a little too small. We would like to move further south from the city to be closer to family. I feel that my luck has run out a bit from the good old days of buying REOs in the Great Recession that any dumbie could have done. 

Essentially we are into the house for 405k and I believe it could fetch 399ish if we we’re lucky. Losing more money selling it doesn’t seem like an option to me right now. The idea has come to mind to rent it out and continue on down the road looking for a better buy. I have toyed with this, but I would be completely new to the landlord side of it. My mortgage is $1650 all in and I believe it could fetch at least 2100$ safety for rent. We would in the meantime I assume rent a place and continue to save and get setup to buy again. 

I feel dumb luck has run out and now look for real advice. Probably a long winded intro and please let me know if I should repost in a more specific thread. Remember I’m new!