My initial goal was to have property where I don't have to pay for a mortgage out of pocket due to lay-off risk in my job.

When your rental income and deductions are on Schedule E you deduct in the year you pay, period.3) Read through the IRS Publication in Rental Income and Expenses make sure you are keeping records and deducting everything you can. https://www.irs.gov/publications/p5274) If you spent 250 hours over the course of the year on matters relating to the properties you can take the QBI safe harbor which deducts 20% from your final after-expenses number.There are other areas to look at in your tax picture that can impact the amount you pay over (your top tax bracket).

I think I am looking for someone to do taxes and give tax advice but I am 52 with a great job and would like some advice for investing / retirement planning. 

---REALITY: tenants don't want you in their home while their packing to move.We try our best to schedule a MoveOut Evaluation the day after tenant moves out.

On the same note I have tried to get her to invest in other properties with me and she is terribly risk adverse and just can’t stand the thought of having her name and credit being attached to a large mortgage even though I have explained numerous times about how the bills and mortgage payments are made by the rent payments. 97% of the time she continues to be supportive of me pursuing the real estate on my own and has been supportive of me retiring from my job to pursue it full time.

@Ruchi Patel if the walls need repair from damage, like painter will itemize special primer or cleaner so crayons don’t bleed through, then my understanding is you can charge them for that part of the job, but only if it’s an additional charge above the normal paint job fee.

Unfortunately, that is when greed set in and it was voted that we needed to expand to other locations because our business plan was getting behind schedule.  

Then, depending on if you or your wife have a traditional day job, you'll definitely want to consider making estimated payments to avoid underpayment penalties. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with zero or negative relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560, little to no good tradelines, lots of collections & chargeoffs, recent evictions.

What did you do for your 9-5 job?