Selling, Renting or REFI in this market

[Jonathan Hudak]

I'm basically a "Pre-newbie". Have been following Bigger Pockets for a while and am looking to get started in Real Estate in some fashion.

My wife and I currently live in a condo that we own (bought for $255k, currently owe $165k @ 4.05%) and the current value seems to be between $300-320k and has never been higher. We're in an expensive market in Fairfield county, CT. 

We're currently weighing options:

1. Selling now and moving on with our equity to buy a new place

2. Buying a new place now and renting under our current mortgage. Cash flow here seems tighter; $100-150/month if we hit expected rent.

3. Refinancing to new 30-year fixed (would be 2.85% w/ 6100 closing costs rolled in), with the goal of buying a new house and renting the condo out in 6 months-1 year when/if the market softens. The number seem to work out to a palatable cash flow of 300-400/month with this refi and lowering our payments, after accounting for capex/repairs and not including property management. We did consider a 20 year REFI option but with the extra payments the cashflow is much smaller, and the 30 year with extra payments came out very close in terms of total $ saved over the life of the loan, with the added flexibility and smaller minimum payments.

Looking for any feedback or suggestions as someone who's just getting started a little later in life (37)!

-Jon