I’m looking for advice and firsthand insights on operating a self-managed short-term rental (STR) in North New Jersey, the Catskills, Hudson Valley, or Delaware Water Gap areas.

A lot of my clients buying in FL are happy with minimal return but are buying for second homes, tax benefits, etc.I would stick with value add - with refi you can still achieve high CoC and a good equity position. 

Cons I would say are achieving financing.

As someone born and raised in Cleveland, I've witnessed the tremendous growth in Northeast Ohio firsthand.

If you’re not paying cash for properties, get pre-approved for an investor loan to understand your available credit.Time FrameThe shorter your timeline to achieve your goal, the more upfront capital and credit you’ll need.End GoalMost investing goals focus on replacing their current income, like $5,000/Mo.

I'm entirely new to real estate investing, but I have a high risk appetite because I have seen other people achieve amazing things that many say cannot be done.

However if I do a BRRRR I can achieve infinite return by extracting all of my investment.

I am learning that firsthand as well and honestly, you just have to take it for what it is. 

As you mentioned, it might be difficult timing the sales of each of properties where you can achieve a combined exchange (multiple properties into 1 property / or a few properties).Just a quick note that may be helpful - I work with a group of investors that can help with a combined exchange into a single property and will buy it back once you've found a replacement propertie(s) as the final destination for your capital.

High occupancy isn't sexy, but that's what a good property manager will achieve, plus it's much easier to maintain a property with the tenant's money than the owner's money.