I have a confession: my only duplex, which I gave owned now for 2 years and recently moved out of from a house hack, has proven to cost me more to maintain/pay taxes/repair/fix etc to the point where my cash flow is close to zero.

Just so you know, Vrbo and Airbnb will not allow you to receive an inquiry through their platforms, and then take the booking off-platform, they want their cut of the money. 

I have the money to buy now but I would rather do creative financing and use as little money as possible out of my own pocket. looking to start with BRRR method but maybe should start with a wholesale first to fund that?

CT isn't cheap so if you plan on doing it there you are going to surprised at how poorly you do. maybe in the suburbs I'm not sure but as much as I know people call us from CT and everyone is rich and has lots of money and things are expensive out there. build to rent is a great model. we build 3 story walk up infill and keep it to the residential side. 3 units is the most units before it's commercial and you need engineering, etc. check comparable and things liek that. we came up with this design a year ago and we sold 10 if you want to talk further please DM me happy to connect. there are some great build to rent conferences. we went vertical not horizontal with it to save on build costs and design to fit on any infill lot. this fits on a 3500 square foot lot. most lots in our area are 30x120 or 30x150. in miami where I live now they are 50x100 or so. but any infill lot we can pretty much get this one on. there are some great build to rent conferences coming up too that if you like this topic I'd recommend attending I'm sure you'd learn a lot.  

Tenants save money when using a shared meter, so there's plenty of room for error when calculating how to distribute the charges.

With it being that risky, the least I could do is have some money saved up.

If you can get a better primary residential HELOC rate than you can a hard money bridge loan I would say yes.

That’s how I got started—with little to no money out of pocket.

Also, these people have been collecting unemployment with the additional $600 a week federal money for 4 months and never bothered to pay any amount towards rental payment (money which we pay for in tax) and they get for free.

In California there is $800 franchise tax per LLC per year, which discourages a lot of RE investors from getting an LLC.