I'm torn and eager to dive into another investment that will cash flow year round. 

Something to dive deeper with a financial/loan professional.

Unless you've got deep pockets, a thirst for the edge, and are lawyered up it's probably not something you want to attempt. 

I worry that a disgruntled renter could see potential deep pockets if they did their research. 

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?

I would be so deep in the red.

.- If you hold a rental until death, you can pass it on with a stepped-up cost basis, limiting captial gains if then sold (limited by inheritance tax limitations).Too many newbies on this site trying to replace their day job income via "passive" real estate investing w/o digging deep enough to understand how it really works.

👋I work with a lot of investors who are diving into short-term rentals, and I wanted to share a few tips I’ve picked up over the years that can really help maximize ROI.

And then again, maybe I’ll dive into both simultaneously since I feel very confident from experience now.Like @Michael Baum Baum said, guests from both platforms can be quality (I vet to ensure this).

My takeaway after more than a decade of experience is that Section 8 can be an excellent way to diversify your portfolio, but I wouldn’t recommend relying on it exclusively.If you have any questions or want to dive deeper into the specifics, feel free to reach out.