I figured if I was going to owe Capital Gains, a HELOC would make sense since you don't have to pay Capital Gains on debt service.

I know there is surety bond process and there a a few companies that appear to offer a service (Like Rhino)Furnished Finder has a new feature called Worry Free Waivers but when I tried  to better understand their process, it was clear they have not done a good job of vetting this out. 

A tenant living in a 100 year old called board of health for drafting windows (never called us first) and BOH made us replace them within 30 days, well custom windows take longer than that to make so we got fined.

Usually the type of work has to be dealing with the real estate itself, not just providing a service that is applied to a part of the house/building. 

Were there any challenges with shipping, customs, or delivery?

If you want these types of service, then you should should look at the pay structure to see if it makes sense for all parties.3.

Again, I’m not sure if these guys do this to everyone or if their customer service ability as partners is just terrible.

If you're looking at a debt service loan, 15% is the minimum for a purchase but it's much more common (and rates are better) at 20-25%. 

If you provide excellent housing and excellent service it is likely that your turnover rate will be lower resulting in less future vacancy.

Quote from @Natalie Allie: Hey Michael, I am in the Detroit area and work with investors for PM services and renos.