(Mid to late twenties, working professional, able to pay rent but not quite ready to buy a home, I would feel comfortable managing them etc.).

Therefore I lived with family while working 70+ hours as a residential plumber until the age of twenty when I built my home (the SFR I mentioned above).

I can overlook credit issues from an early twenties person or things that go back more than 5 years. 

Twenty years experience investing in the US (Boston).

My wife and I are making our first step from getting out of our early twenty mistake of buying a luxury home with land and moving into a house in downtown Colorado Springs.

In some of these markets, properties sell for $50,000, but they sold for $45,000 twenty years ago.

they were my late night driving companion as we came back from vacation this week 😀).I'm a twenty-something husband and father of 4 working full time as a software engineer at a non-profit.

And plan for the refinance to drag out a bit as the conversion must be thoroughly documented twenty ways from Sunday.Worst case: is this going to bankrupt you if after jumping through all the hoops and red tape, the answer is "no"? 

However, I think everyone here realizes that $300 now is certainly not worth $300 twenty years from now, when maybe I decide I'll retire early.

What are some tips for someone as young as twenty starting out?