Once the property is rented out you can refinance and pull out most or all of your cash. 

They are often motivated only to keep the monthly fees low, which they accomplish in the relatively short term by deferring maintenance on items they feel are less important, and by "saving money" using unlicensed and often poor quality vendors to make improper or inadequate repairs.

Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion.

You are actually financing part or all of the purchase with you money, it is a use of funds matter.

For Auctions, or foreclosures/pre-forclosures/bankruptcies, should I have an attorney involved for the first one or two (or all of them) to have the legal guidance?

Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion.

I've made multiple offers this year, and I've lost on all of them, either to higher bids or all cash bids.

They will attempt to get the seller to covers some or all of the repairs but assuming they didn't pay anything the buyers purchase price in this example would be $490k or a saving of $10,000 off the asking price.

NO ORAL CHANGES OR REPRESENTATIONS.

It may be more capital and time intensive up front but it creates a scenario where even in San Diego County you can have an opportunity to put in sweat equity, get the rental revenue potential up through renovations or create new rental revenue streams with an ADU (or both) so cashing out some or all of your money out after doesn't have to leave you with negative cashflow out the gate.