If you're looking for a more landlord-friendly market, I personally recommend Columbus OH.

What appears to be great "curb appeal" to one person might be overwhelming to another. 

So on numerous occasions, I have expressed my concerns about staying within my budget.Now on top of this, the property manager let the pipes freeze and they leaked and the boiler also cracked which I was told to file an insurance claim.

Personally, I do not like any strategy or approach that aims to benefit from the misfortune of others.

The 5-10 it gets heavier and a lot busier, and 10-15-20 it really is untenable to self-manage especially if this is not you main business like a person buying their own rentals and building it like a small business. 

It's a matter of finding the one where the weaknesses are in areas that aren't relevant to your needs and/or don't aggravate your personal pet peeves. 

I want to start smart and scale up as I learn the ropes, but I’m personally struggling to narrow down which area to focus on.If you’ve done this before, what advice would you give someone like me?

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?

Caution:  Personal credit card financing is a huge risk and good luck finding 0 percent interest today.

HELOCs are generally provided to properties that are held in the owner's personal name.Are your family members not interested in refinancing the property?