I know the general basics of the market, the business model, etc, but I was hoping to take my knowledge to the next level.My biggest goal right now is to own a rental property before I graduate college (currently a junior in high school).For context, I love reading books about investing and personal finance (I have a very solid foundation of knowledge built up) and I currently have a portfolio of about 11k between stocks and crypto. 

What are the biggest challenges people face when underwriting a deal? 

I invest using BRRRR and what I've seen lately as the biggest obstacle to that strategy, has been the initial hard money lenders, with the recent market changes this past year are doing lower ARV percentages ...example going from 80% ARV down to 65-70% ARV to mediate their risk, requiring more out of pocket initial money's. 

The biggest issue we are running into at the moment is finding a profitable multi-family unit and how to fund it.

Some people treat their STR like a hobby and others treat it like a business.You don’t know the numbers are based on if owners use it 3 months a year themselves, or manage it themselves and have STR knowledge or farm it out to a competent or incompetent property manager.In one area I invest in, the biggest players are all large direct booking sites with hundreds of properties so their revenue doesn’t show up on airDNA, etc.Use conservative numbers and understand your skills in terms of getting a property to be unique, marketing, listing management, etc. or the competency of the PMs you are interviewing.Good luck!

This was my first deal with a 30 Year fixed mortgage and the paperwork was the biggest challenge.

Biggest advice I would give is get out to real estate networking events!

Or, a charging order may be granted.If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

If you have generally good tenants who pay on time, that's the biggest hurdle.

The biggest disadvantage is not being able to do a cash our refinance correct?