The quality of them PM is one thing, but it only gets amplified by the quality (or lack thereof) of the properties and the resulting quality of the tenants.If you were to illustrate this with math it would look like this:  0.1 x 0.1 x 0.1 = your result.The answer to your question is obvious, but frankly easier said than done: buy quality properties with few repairs, they will attract great tenants with few issues and even a mediocre PM will do just fine.The allure of cheap cash flowing properties is real: After I had invested all my original capital I bough a few cheaper properties in Milwaukee (this was around 2010, so they were really cheap) and fortunately traded out of them within a couple years - it taught me a lot!

Your CPA can do this but they must ensure they follow the IRS guidelines and either employ or act as an independent third-party certifier.Can I apply for this deduction regardless of how much I spent on upgrades on the building?

Profit from flips are taxed as active, ordinary income which includes self-employment tax (15.6%). 

You get that first paycheck and notice your employer automatically took out a portion of your salary and create you a brand-new 401K account.

Repairs and maintenance aren’t a big deal as we have folks employed that handle most of it.  

I once got references from someone who was 63 and all his references were from his past employer.

Her mother still lives at the house we’re buying and we want her to continue living there for many reasons, but a big reason being that we employ her as a nanny.  

Site and features make it a 10M parcel with gradual development in 10 years (could flip for 3-5M immediately with the right marketing)B) Standard downpayment (240k) 1.2 mil - house - rental income would be about 3500 initially, with ridiculous business potential (currently unrealized/undeveloped)This isn't a planned sale, and being self-employed I've maxed write-offs and minimized income so my income probably won't cover the mortgages needed in the bank's eyes.

It does not mean we can.If you have a W2 job which is part-time, let's say 25 hours per week, you will need to be able to have your employer confirm it in writing.

I highly recommend employing an experienced RE attorney to draw up these documents for you.