If in the rare chance they do allow short term rentals in the HOA rules/regulations and association documents, don't be surprised if they change that ruling after you buy. 

Before listing it on an STR platform, I need to make some improvements to my current home.How can I maximize tax write-offs for these improvements?

At my point in life everything I own is both a cash flow superstar and appreciating nicely, because I'm invested in growing, popular areas.If I was just starting off now, I'd probably be aiming for value-add in good areas where I could either live there while improving the unit(s) - ie a duplex, triplex - or where I could trade sweat equity for profit, or both.

Because, if you are a “regular” person meaning don’t make 5M a year W2 / legit bussiness which shows on tax returns, you can’t qualify for 20M loanAlso it mean, that people who buy 20M condo, chances are they have 100M-200M cash sitting and not doing anything.Return of equity is 0, as it also the cash sitting in a bank.Debt is cheap now days: 4-5%, but if you have “unlimited cash”, then not need to pay 4-5%As far as max cash flow and minimum risk - it’s something a lot of members discussed already.And last but not least - let’s not go off topic.

I initially accepted it as an improvement.

I'd go ahead and list it.There are many past posts on how to improve your search list placement such as making frequent changes to listing and updating pictures.

It's very important to have a good PM and not go cheap or there's a high chance your rental will get poorly managed and you'll lose money in the long run. 

What you need to do is show what compelling argument makes taking this chance on you make sense. 

If I had the chance to buy in 07, 08, and 09 I would but I was in high school.

Quote from @Robert Gunn: I would also be very interested in hearing student or JV experiences with Pete and his program.I stumbled upon him by chance and for fun (I've been investing in land for years) signed up for his "free" course, which he promises after he pitches his $499/mo software system (which is basically an overpriced CRM) and then after the first "Level" in the course, you are directed to a pay page to access the rest of the "free" course.