Definitely recommend checking out local REI meetups in Boston now and Chicago later—tons of value in connecting with local investors.

What are the pros and cons of this approach?

Id let them out of the lease or evict.

@Christopher HeidrichRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

When I asked him where he gets his deals from, he said wholesalers, word of mouth, and bigger pockets.

You cannot rent out an entire home/apartment for fewer than 30 days.Your STR must be registered with the Office of Special Enforcement.

***BUT keep it ***B - Buy it F - Fix itLive - Primary Residence itLeave - Keep it, rent it out, and find a new primary residence What made you interested in investing in this type of deal?

The connection happened in less than a week of listing but I haven't seen anyone talking about them.

We have zero concerns of squatter in SWFL.

Quote from @Adam Macias: Wholesaling as it is today will be a thing of the past.It’ll truly be strange to even hear people and gurus trying to make big money off it.The more people try wholesaling but then end up not having an end buyer or cancelling contracts or trying weird things like novations, the more all of real estate will be regulated and cause requirements like licensing to be able to transact more than just your personal resident purchase.Which I don't know why hasn't happened sooner.Here's all the states (in red or yellow) requiring a license to wholesale or at least have started the process:Credit: REITipsterI think licensing and regulation is a beautiful thing that should happen if you plan to be an wholesaler and do more than one deal... which is going to be the case for anyone taking this business seriously.Or even it being regulated to need a real estate agent to do more than one deal outside of buying a personal residence.I've had plenty of failed attempts with agents in pursuit of wholesale deals and I know exactly why, it's not because the agent couldn't find me deals, it's just not practical to think there's opportunity for the numbers a wholesaler needs to make a profit on top of everyone else needing to these days.Because the only sellers who truly can sell at a deep enough discount are usually those who ran out of time and just didn't do something sooner with their situation.I know many coaches and gurus will disagree with me but there’s no regulations on youtube gurus and what they teach either.If we look at the current state of the market in hot cities, the availability of online resources to the average homeowner, how many deals can you possibly believe are available at 70% of ARV?