I’ve been there, and I want to share insights that can save you from costly errors.During property tours, ask smart and relevant questions.

Arguing never works.Get a good attorney that specializes in landlord/tenant law and accept that it will at times cost money to have them deal with things.

I know I need to up my game and start investing if I want to make a dent in those bills.

Whereas I don't know if it will make up for the cost of software when only renting. 

If you were not, you’d save the same taxes as strategy 2  Or 2) You’re going to spend money (capex) that will be added to your cost basis giving you a higher yearly depreciation.

If you are looking at this decision through the investment lens, what would you net on the investment that you put this money in to, after transaction costs and taxes? 

Let's assume you don't take a loan.Purchase Price: $1,299,999Closing Costs: $25,000Renovate unit: $35,000Build 2 ADUs: $250,000TOTAL: $1,601,000The cashflow calculation looks like this:Gross existing rent: $5,600Gross rent from 4th unit: $2,500Gross rent from ADUs: $3,000TOTAL GROSS RENT: $11,10020% Expense Ratio: -$2,220Property tax: -$1,354TOTAL EXPENSES: -$3,574NET CASHFLOW: $7,526So, about 3/4 of your $2M budget gets you to about 3/4 of your $10,000/month goal.

Food cost, Insurance cost, Drinking cost, eating out cost are all going up.  

Decide which game you want to play.

Condition of a property and the cost to repair is just one of the risks in this business and you have to consider that in your buy price.