Keep in mind there are density bonuses available such as TOD, Green Roof, etc. that can potentially increase density but they're harder to come by. 

I was able to move into the largest "bonus room" upstairs and rent out the other four rooms for $500 each, totaling $2,000 per month.

As a capital expense, it should be depreciated --- and then you could try to use the bonus depreciation (is that sec179) but then you still don't have any income to offset.Either way, you can't take the deduction immediately. 

My entire family lives in the area in which I'm considering buying, which is just a bonus in the fact that they could drive by - otherwise I would obviously look to outsource management of the property.

.- A project manager's should be paid a flat fee (with or without bonus) such that their interests are aligned with yours to make the most profit on each deal.Let’s get to the meat of the matter: A project manager working for an investor should have no incentive to use substandard materials or subcontractors.

The cities in CA are often viewed as an appreciation play.My personal advice for you would be to house hack your next property for 2 years, look for something that has a bonus room or opportunity for a value add.

For a rental adding central AC in south Philly is a must so a house with ductwork in place is a big bonus.

Since conventional lending is not in my future for several months, I would be looking for subject-to, seller financing, and/or hard money, depending on the situation (still learning more about those).Naturally, going where the numbers make sense is my priority, but it would be a nice bonus if it were somewhere I myself would like to go or could realistically drive to in a day (or hop on a quick flight to).

Since we are young, our salaries are low by bay area standards, but we both have good care trajectory and make a combined $155k gross, plus commission bonuses.

The reason why I wanted to do a cost segregation or at least see if it makes sense for us is because I want to “ use bonus depreciation or try and get a refund back to use on another property and of course save taxes.