Chase Bank told me that they do setup accounts at the series level. 

You'll definitely get the long term appreciation in the San Diego market since our supply levels remain low which helps to insulate our market here, but it will be hard to cash flow on immediately unless you use one of the above strategies I mentioned. 

3) It's been 5+ years since we've seen a S8 tenant lose their voucher for property damages, not paying their portion of the rent or utilities, or other lease violations (letting others move in with them).It's our opinion that #2 & #3 above are caused by overworked caseworkers not having the time to process the extra required paperwork, so they take the path of least resistance.4) S8 needs someone at the federal level to put more of the program online and streamline the process!

This has affected me on an emotional level far deeper than it has economically. 

Here's a link to the data: https://mred.stats.10kresearch.com/infoserv/s-v1/vwxv-Zs5What this data shows at a Macro level is that the Chicago market is doing fine, but the market is too large to use that data to make any decisions about where you want to house hack.

Hopefully as the rates and the housing market loosens so will some of these guidelines in the HML programs. from talking to hard money funds especially those who operate in more than 10 states, and 5 years of experience with underwriting teams, I'd actually disagree and say new construction is preferred to rehab due to experience level to enter the market. there's BP lenders that will do 15% LTC with 1-2 new build experience.

Quote from @Anthony Dupre: @Chris Seveney Would you mind sharing a high-level overview of the structure your billionaire friends have set up?

They will give it to them and then convince them a 10k course will take them to the next level.

It would simply be another level up from the LLC taking title.

There will always be a level of fear of failure and you will most likely experience some, mitigating that with diligence will keep you in a healthy state of paranoia.