I've invested a few thousand into my education on the topic, and invested a ton of time over the past 5 months- would it be a really bad decision to stop wholesaling and just try to save up for my first rental?

There's several thousand cabins where i am, in a vacation-rental-only/tourism part of the world.

Trying to save a few hundred dollars in closing costs is just absurd if it is going to cost you the deal altogether, or cost you potentially thousands of dollars of leverage in home inspection negotiations.I will say though that Ive had a couple transactions in the past year where using a bad professional helped.  

Investing in a market where you have no knowledge, no control, thousands of miles away, that has less competition and less demand for properties (which is why they are cheaper and appear to cash flow more day one), and where you will be 100% reliant on strangers to make or break your investment for you, with the thought that will somehow be more profitable doesn't sound like a strategy worth pursuing at the moment.

-Throughout the years, tenant has consistently been rude to other family members (also owners) and consistently makes baseless claims that they spent several hundreds of thousands on remodeling the unit and changing floorplans (explicitly stated in the lease that this cannot be done without our consent) and has to always make the last point, regardless if it is reasonable and/or valid.

Since then, we've directed millions of TIF funds, hundreds of thousands of dollars in aldermanic menu funds, and over $500k in private funds to our neighborhood schools and high schools.

I was quoted several thousand dollars to re-wire the property 'split' the power, so I didn't really want to spend the cash.

Although, technically it could be done, the reality is that you will need to spend money, possibly thousands and thousands, to find the motivated sellers. 

Enter: The inevitable guru pitch, which suggests that if you pay the guru a miserly thousand or three, you'll be given all their no-money-down secrets!

Not alot of people realize this, but if you sell for $40K less than the property is worth, be prepared to be sent a bill for the $40K after closing AND be prepared to be sent a tax form to treat the $40K as INCOME on your taxes for the year you sold it (which TOTALLY RUINS YOUR DAY!).