@James CasellaGreat job on gaining knowledge.

Finding a fixer upper can be the easiest way to gain appreciation.

I am looking to inject (contribute) some money into one of my LLC to finance some new acquisition this year.I am refinancing my home (that is under my own name) and will use the cash out as contribution into the LLC.It is my understanding that while you can't deduct new mortgage or refi anymore on your personal home, you can still deduct all its costs when it is used for investment (by deducting from the investment income/gain).What would be the proper way to document this transaction in addition to the schedule recording the contribution in the LLC book?

Lower capital gains tax as compared to income tax What made you interested in investing in this type of deal?

We needed a family home and wanted to find a fixer upper to gain equity.

We needed a family home and wanted to find a fixer upper to gain equity.

You'd need to wait months or years to pull out a good gain unless you do a stellar rehab.Any method of investing carries risk.

My goal is to find a -plex or handful of -plexes in my hometown in order to gain experience and just learn the ropes, and ultimately scale into the Springfield or maybe KC markets and beyond.

I love it too and I never thought about the screening aspect, however it's my assumption that most gainfully employed biz professionals will be good tenants (more or less). 

If so when you SELL the home you can deduct up to $250K each (husband and wife) from the gain of the home and NOT pay any taxes.