@Liliana Bennett most HOA boards are composed of the actual homeowners.Just like there are many DIY owners here on BP, trying to pinch every penny, there are HOA Boards trying to do the same.Guessing your HOA Board members have specifically taken many possible tasks away from the PMC in an effort to save money.

I'd say the Bigger Pockets forums are one of the best places to explore how to put your money to work in RE. 

Should I feel bad if the lender spends the money on the title search and I don't use them?

If you are uncomfortable investing your own cash, how will you convince others to invest their money?

I’ve got a distressed and on-market house that was recently completely renovated until the couple ran out of money (all of the heavy lifting has been done, just a few things left), and it is listed well below market price compared to surrounding comps I could find.

I did learn a lot and was inspired, but rubber hit the road and I ran flat *** out of money. 

,...the one that makes  you more money. 

I'm wondering if there is a typical amount to put down as earnest money?

Quote from @Aroldo Gonzalez: If you borrow money from your current property, that will increase your debt and reduce - and possibly eliminate - your cash flow. 

If your potential numbers already look good, you most certainly won't regret the money spent on a designer!