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.

Here is a question that we have not dealt with previously.  We are looking at a property that has the typical old interior stairs that are just short of being a ladder (reminds me of Navy ship stairs).  There is room ...

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? 

But the no up front cost option is great for basic updates and upgrades for a retail home seller.

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.

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.

Financially speaking, I'm still saving, but the goal is 50k saved up (all costs: closing, fees, down payment, portion of rehabbing costs) by this summer with my fathers help on the cash all while I continuously save 50-80% of my work checks to fund for rehabbing this property and I work off my second job and "survive off of that."

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. 

Very little out of pocket cost.