My understanding is that the ballpark standard of "unless it would be outrageously tough" (something along those lines) is what applies if you're doing a rehab, seeking new permits, doing structural changes anyways, and things of that nature.For existing pre-ADA structures, my understanding is that the standard is more along the lines of "if it can be easily/cheaply done, you have to do it."

For example, $50,000 loan at 10% paid out evenly over 10 years.Like I said, super new to this part of the business, so trying to wrap my head (and spreadsheets) around it.

Hard to produce cash flow or break even with that much debt, at that rate.House-hackers, however enjoy certain one time (non-scalable) advantages that should be taken advantage of in the early days: - They can assume pre-existing debt like VA and FHA Loans (rather than take it on Subject-To which is dramatically riskier).- They can rent by the room and self-manage to produce day 1 cash flow.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

Honestly 350 days a year I don’t even think about it. 12 days a year I wonder if everyone paid and if not will they pay, for about 30 minutes.

They'd be much better off being a Hard Money Lender and make 5 times that (and every repair to their "investment house" is paid by them...So, if you put $10k down on a property and make $150/month net cash flow your Coc Return (annualized) is 18% which is Very Good.If you followed that and understand it then keep looking for a deal.

Even if you get something in escrow right away, it's still a 30-45 day escrow period before you would get paid, unless you are working with cash Buyers.  

I am expecting to do 3-4 deals per year until I get to 20 properties or so and then snowball the debt so they are all paid off by retirement. 

Additionally, the estimate for my tax preparation for this year was approximately $1,000 over the cost I paid last year (including the time I paid for them to correct their errors).

An update one year later after this post, I now have:- Got my property and casualty license and wrote 370+ policies in a year- Saved up a few more thousand dollars in investable cash, paid off $20K in debt and raised my credit score by 100 points- Launched a direct to seller cold email marketing campaign and generated leads for cheap- Got connected with a few real estate investing communities like Subtle Asian Real Estate and Pace Morby's SubTo- Aggressively read and studied as much as I can get my hands onThat being said, I decided to run a marketing campaign to generate distressed seller leads in Phoenix, Arizona, mostly because:1.

From what you wrote it sounds like the rental you own is your sole, pre-marital property.