I am not as concerned with cost and would prefer quality and transparency.

Also, please bear in mind costs; some states could have annual fees for an LLC in the hundreds of dollars (e.g., California),  whilst other states have no such fees (Texas).

A simple mistake can cost you more money or time.Here's a pretty good guide: https://www.clarkcountyohio.gov/DocumentCenter/View/5210/CCO...

For me I’ve found the lower cost to entry to be more desirable in the residential market.

As the seller I would pay for the energy audit, do the analysis on the work to be done (cost vs savings) and then market the home with a prepackaged improvement contract that would meet lender guidelines (solar, EE windows, etc). 45 day close to allow for enough time to do loan and obtain permits, occupancy COE+2. 

Does it usually cost money to have a contractor come out and do this?

The right locations are crucial for our success, affecting costs and member satisfaction.

Why would he prefer a $1500/mo (150k-purchase cost) 2 BR 2 BA 1000 SF condo over a $250k 4 BR 2-3BA 2000 SF house where we rent out half and live for like $500/mo?

You could consider doing a cash out refinance of your current primary as an investment property with a dscr loan.From there get a low cost or zero down loan for your Primary.Use the proceeds left from the refinance to get your next property.There are so many different strategies.

Appreciation tactic is a tough one to start with as markets can stagnate, and you end up with a property that ends up costing you maintenance, but only covers the mortgage or is negative.