I have a problem with financial advisors as a general rule, because most are sales people trying to earn a commission. 

STR income isn’t considered passive if you meet material participation rules, allowing STR losses to offset W2 income.

They'll also change they rules because they don't want to mess with, count, hold on to, $1,000,000 in cash, so they'll switch it to cashiers checks. 

I'm getting to the point where I have a good chunk saved and am wondering what guidelines people follow to know when they can start tapering off the contributions or stop them altogether.What rules of thumb are out there that people use?

I even have a friend who received an unfounded complaint from a neighbor (the neighbor was just against STRs, no events/parties that occurred), and now their property is temporarily banned/under review, regardless of them abiding by all rules.

It sent some messages with house rules  that didn’t sync correctly, pulling in info I had already updated on Airbnb.I only have one property and wanted a PMs that:-took direct bookings-synced calendars - completed simple auto messaging I like the idea of a PMS but I really don’t want to spend a lot as I’m also using Price Labs.

In case your expenses are more than your income, you come under PAL rules.

Since you already have an S Corp, it might be worth talking to a CPA who knows Pennsylvania rules to see how short-term rentals fit in.

@Jasmine VidaIt's hard to say, there is no hard and fast rule.

So I was wondering if that is a new rule that I just never knew about.