So to make sure I'm understanding this right...If we put aside the decent salary from the PM business (and again, congrats on creating a successful business!)

My sister has a decent portfolio in Denton, TX and over the past 3 years her taxes have gone up 100%+ across her entire portfolio.

Also you have locked in to a low rate and currently have a decent cash flow.

Hi all,I'm a software engineer at a fintech company making decent salary.

: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+ (roughly 5% probability of default), 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 (around 10% probability of default), 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.

You are required to file a complete and accurate return, which means reporting the income that you earned along with atleast the direct expenses that you incurred on your rental.There are two comflicting forces - Your tax accountant wants to be aggressive with deductions because it will entitle you to paying less taxes(now or in the future).Your lender wants to see as much income as that will increase your Debt to Income Ratio(DTI).The good thing is that you can speak with your lender about 'one time expenses', that were only incurred in that year and are not reoccuring. 

Used decent envelope printer, $7,500 (lease for $250 per month for 39 months).  

There are plenty of people that for $100 will use their medical license and type up a letter that their patient needs an ESA.Also, if the ESA exhibits any aggressive behavior it can be removed from the property IMMEDIATELY. 

Any decent lender should allow you to borrow against your airbnb, without disturbing the original 2% loan.Example: I have a 6 unit that had ~$500K in equity.

Additionally, since you need to replace your vehicle soon, you should consider how that $30k purchase fits into your overall budget.Take a close look at the current housing market in Orlando, where prices are around $400k for decent homes.