Assuming you can afford a mortgage, and the other costs involved, and your job is not in danger of being cut, then yes, now is a good time to buy.

Credit rating, criminal background( check with state laws on this).Pets vs. no pets, list of dangerous breeds not allowed.....We have list of qualifications that we give to prospective tenants BEFORE they fill out an application.This way it saves everyone involved time and money,and you protect yourself by treating all interested parties with the same guidelines.

You are in danger of entering a downward spiral that looks like this: the owner can't fill vacancies bacause your units are unattractive, cash flow is down, owner hesitates to improve units, pushes PM to fill units anyway, so they lower the standard which leads to much bigger and expensive problems including ecivtions.

Less money in my pocket but fewer headaches too...

I manage 400 rentals and fewer than 1% leave owing more than their deposit will cover, but that doesn't mean the owner has lost money.

Challenges are living in a very expensive winter resort area with few available, very expensive contractors, and even fewer willing to take on remodels. 

This would be a cheaper approach at the outset.But like @Kathy Henley says, you may be better off counting the costs of an operating agreement among your start-up costs, and being confident that you're doing it in a way most likely to have fewer problems down the line (nothing is bullet proof).One key thing to recognize is that the attorney is helping you predict potential future problems and plan for them now; but he/she is not deciding anything for you. 

The gym would include "dangerous" equipment like free weights.Let's assume I'm reasonably paranoid about liability lawsuits, etc, but want to stay grounded in legal reality for this question. 

I know just enough to be dangerous and am looking for some input on a potential strategy I am working on. 

It's riskier, listing agents have to be much more creative with their online marketing and documentation, and the buyers are looking at fewer properties overall.