We have hail storms in Dallas so it seems like a 20 year roof rarely makes it to 20 years....maybe 1/2 that.   

Appreciation alone is riding a very slow boat to retirement. 

I hear that’s a safer bet than doing a home mortgage equity line.Question is should I ride it out and move into my already paid off condo when my tenant’s lease is up in Dec or strive to go forward and invest in a new property, live there a bit, then find another tenant and  replicate once I’ve saved for another down payment?

Quick access to MLT park & ride and soon to be light rail!

Adam, insurance options in areas with Wind/Hail exposures have become limited.

It doesn't give them a free ride in the future.

Hail dent repair, pop-up insurance claim adjusters and dead storage are usually good bets for this scenario.  

Debt FundsPro: More stable deal as long as they did go high LTC Con: Have to be patient and long term player and happy with low returnsPrivate:Pro: Can be stellar returns Con: Need to have a strong heart as there will be a bumpy ride and losses. 

The big question, in my mind, is do you have the stomach to ride out major dips, downtrends, and volatility in the market like we saw earlier this year?

I am a fan of commuter towns/cities within a 45 minute train ride to NYC.