Is it typical for a buyer to take on seller and buyer closing costs/ fees when doing a seller/ buyer transaction involving a wholesaler? 

The broker who is listing that dominates the market, which is good for sellers typically. 

Another option was using equity to buy a 3rd home with FHA (the first 2 loans were under VA).

-Section8 tenants typically live in properties several more years than market tenants.

This is the simplest option because then you can utilize hard money.

It's a strict 2-year requirement.As for strategies to avoid capital gains on the sale, if your client doesn't meet the ownership and use requirements for the Section 121 exclusion, they might explore other options such as:1031 Exchange: If the property is an investment property rather than a primary residence, your client could consider a 1031 exchange to defer capital gains tax by reinvesting the proceeds into another investment property.Installment Sale: If your client is willing to accept payments over time, they could consider structuring the sale as an installment sale, spreading the recognition of the gain over multiple tax years.Charitable Remainder Trust: If your client is charitably inclined, they could contribute the property to a charitable remainder trust, receive income from the trust for a certain period, and then have the remaining trust assets pass to charity upon their death, potentially reducing or eliminating capital gains tax.These are just a few options, and your client's specific financial situation and goals would need to be considered in determining the best approach.

Test them out, if they aren't good try another option until you find the right fit. 

I have $30k of stock options losses this year (multiple bad trades in a row lmao after making 35k last year off options and sadly paying a lot of tax that cant be carried forward to this years losses).

Contractors typically will not

The house is in a pretty great neighborhood with excellent schools and options to commute to most parts of the bay area and I am confident that I will be able to rent it out soon.