You can also tell a lot by the amount of rent being generated.

I would assume the purchase contract has a clause that states title is clean and there no encroachments.

Furnishings that are easy to clean, along with amenities like high-speed internet and pet-friendly options, go a long way.

Here are a couple of developers you should take a look at Trion Properties, their principal Max Sharkansky posts here on BP, https://www.biggerpockets.com/blog/top-5-markets-multifamily-rentals-2019and Feldman Equities out of Tampa (3rd generation real estate family famous for having built the terminals at Chicago O'Hare) who are among the only ones opening up downtown skyrise office buildings to accredited investors.

No pocket listings = agents aren't even calling for new leads anymore, rising interest rate has nothing to do with an agent's ability to generate leads.If you mean multifamily apartments, 5 units and up, some of those agents will know, but not many until you are over 10 units which are more listed by only commercial brokers which I agree do understand seller finance.

I do not see a need for extra cost or tech not all of your guests will appreciate (i.e. older generations).

The goal is legitimate: due to complex tax rules, you have opportunities to game the system by selling some of your investments and intentionally generating either gains or losses.

If you do outsource, some management companies will cover various things like cleaning, supplies, etc. so look into that as well. 

We don’t plan to leave jobs and live off of the portfolio but have it as a wealth generator aka hedge against future risks

The answer is to value this as any other business generating income, not just stick within the confined box of valuing the real estate only.