Ultimately I think that a BRRRR sounds like the route I want to take, but think maybe starting somewhere else could be less risky so I can get my feet wet first.

A deposit on cheaper ones...I've beeN an Airbnb and HomeAway host on numerous properties for the past 6 years. 

We help clients close numerous multifamily deals in the valley each month and have good pulse on what's happening.Matt

The challenges are too numerous to outline here, a person could literally write a book.

This representation is crucial if you're ever audited.Regarding whether to hire a CPA versus just a tax preparer: Real estate tax is highly specialized, with numerous code sections and rules specific to the field.

They'll have numerous articles and contacts highlighted monthly that will give you an education in itself over time.

I've never managed books for any kind of investor, but I'm a quick learner and excited by the possibility of getting my feet wet in the field of investing. 

Leaving aside if the JV is the best way to fund and assuming its not a scam than the fee is probably a very wise business move because a large percentage of the deals you see are from people who are delusional or are not taking numerous things into account (delays, closing cost, wrong comps, time, etc.).

Search the BP for ADU appraisals to encounter numerous examples.

You just need to close correctly and legally.We have several information and instruction documents we send out for free to anyone wanting to learn.I will reiterate -- no fight intended -- just advising what we have seen, done and developed over the past numerous years.Stay safe out there guysAlan