@Dmitriy Fomichenko scratch the part about being taxed at the capital gains rate, you’re right that it is taxed at income levels, however the rest stands.

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!

Covering a significant portion of my mortgage has been a great reward.Solution: My four levels of vetting have helped me find quality room-renters over the last 18 months.I think you already have the answers to your situation.

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.

What is the appropriate level of cleanliness to maintain during project work?

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

I maintain even break even on valuation (which is rare in SF Zoned areas), the ADU has big disadvantages versus new property acquisition including financing, level of effort, rent control, prop tax being based on cost rather than value added, length of time including length of time from first expenditures to first income, reduction of something from existing unit (in your case existing home lost its garage).Did you see starting next year Mf can add an ADU per unit up to 8 units without any affordable housing concessions?

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.

It can be, but it should not be anything close to the reason for purchase or sale.Sloped lots require a lot of regrading to level them which is WAY more expensive than most people think.

Like I said, I may be new but I am driven and ready to continue learning and leveling up my skill sets.