You should know that stocks currently trade 20-30x their next year projected earnings.

Painting seems extremely high, i believe he is charging you $6/ sq' - cut out the painting and get other quotes for that. do not install Vinyl gutters, get a gutter co. to come in and install seamless metal gutters. does the garage door swing out over the treated landing ?

If I continue to swing financing along 10-30 year terms, the medium-distant future is a real consideration for a buy and hold strategy.

I find painters to be the most over paid trade in our industry.

Have been a big fan of the podcast over the past month, and have been spending time over the past ~3 months learning the tricks of the trade.

If you are betting on appreciation, that swings the equation towards buying another house.

Property eligible for 1031 treatment is property you purchased to hold for productive use in business trade or for investment.  

mid 500's to low 600's across all 3 scores, with almost zero trade lines.  

BTW - I see you are a barber by trade.  

Additionally i will be able to save more money to pay down the mortgage or make other investments.If i do buy the studio i plan to hold onto it around 5 years then sell it to buy a fixer upper 1 or 2 bedroom condo, move in, fix it up, hold onto it a few years then sell it and continue to repeat this process of trading up condos.Does this sound like a reasonable plan?