@Errol Graham you're in a tough position - too small for better software systems, but getting too big for spreadsheets.Stessa may be a decent option, as you should be able to track your accounting so you don't miss something or double enter a bill.Depending on the cost of QuickBooks, you may want to look into Buildium.

I am trying to be positive and understand that this is possible, but I am not honestly seeing how this is easy for others and not me.

I have a nice hi-rise condo unit and I get tons of companies asking if I do MTRs for Visiting Nurses, Tech Professionals, etc.My place is positioned near a number of large DC Metro Hospitals, but since covid work-from-home and recent lift of Eviction Moritorium, I have had few people with jobs, but a ton of people recently evicted looking to rent my place.The one viable group - visiting nurses has been excluded because my HOA will not allow short or mid-term rentals (anything less than one year is a No-No).They claim too many transient tenants cause excessive wear and tear on the property and too many people using resources like the gym, or pool or common areas.I think that's a lot of horse waste!

Don’t put yourself in a position where buying rentals creates a financial hardship.  

Then - once you're stabilized around 90% occupancy - re enter the markets to secure quotes from Freddie / Fannie / HUD / life companies / banks / credit unions.If it's an acquisition perhaps you put short term debt on the property, re-position the asset, then refinance after you're turned the operation around.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

At the current interest rates, 1% ratio likely is unlikely to have positive cash flow at a high LTV.  

I enjoyed the hard labor and comradery that I missed from my Navy days working in engineering.My question is, how do I go about getting more experience on paper without having to commit to an employer/contractor for a long-term position? 

The VA really doesn't like second-position loans.

I have spoken with dozens of CPAs that understand the ruling in the passive loss limitations as @Brandon Hall explains it (tagging him in case he wants to defend his position), and very few that don't view it that way.