I changed my strategy from 2 years ago of acquiring more doors and "cash flow" to now looking at the asset if I continue to buy. 

Im at base pay since I Just started, top pay at this job is at 5 years and we make 100k base pay, there are guys easily clearing 160k due to OT and other extra money functions. we also have a lot of opportunity to move up in position, Supervisors clear 230k like nothing so right now I'm not making much but long term this is one of the best city jobs to work.

If this concept is unfamiliar, then continue to ignore it.In closing: The dangers of shifting the timing of your income, expenses, and business transactions.A purely mathematical exercise may indicate some beneficial timing for this or that.

The departing tenant says she will continue paying rent, but I wouldn't bet on it.

I also purchased a multi-parcel farm property in TN where the trust who owned the property was out of money and needed cash to continue. 

This could create a disdain for flipping properties and not continuing on the path..The other option could be wholesaling it to start a path to build a war chest to go out and do the first flip with your own money down. 

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value. 

I will continue the journey in this thread!  

New to real estate but possess a deep understanding of the responsibilities to continue to gain knowledge and remain loyal with my clients and professionally with my colleagues.  

Some questions I have.1) Do you make enough from your houses that you can not only replace your income but also make enough that you can continue investing in real estate?