We have restricted cities in my market that are loosely enforced, but I would highly suggest not going into an investment "hoping to not be caught". 

My endgame is to end up with $300k/yr in post-mortgage income in 20 years based on investments I make now followed by continued investments over the next 10-15 years own.

I have around 8k saved up and my goal by the end of the year is to close on my first rental property!

So end of day you are in it for say $305k.

He markets himself to no end and I see more stuff from him than anyone else, but he is one giant sales pitch. 

What did you end up doing? 

Many of my clients are high W2 earners who are taking advantage of the "STR loophole." 

Let's assume the financials in the package are good for a moment (they probably are not) AND that you either do not or do achieve the broker's pro forma:If you purchase this asset, achieve ONLY the 'current' NOI, grow NOI 2% per year, and exit at a 5% cap at the end of Year 6, you will have a 4.8% unlevered IRR. 

It’s all good now and this was just a question since it related to repairs but ended up being a seller credit instead of my coming out my pocket to do repairs.

I highly encourage everyone to view the property before putting money down, but that's not ideal for many of them, so I do allow them to rent "sight unseen," but I am very open with them to ensure they don't show up and back out.1.