Do your own maintenance items and reduce maintenance/cap ex costs.  

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.

These changes have reduced the market value of real estate significantly which caused Dave to owe more than what his properties are worth.

Will reduce this reserve number given that.Thanks for helping!

Also might be a good idea to look into section 8 to reduce turnover as much as possible because that really is a killer over the long run.Happy to connect and talk more about house hacking in Philly!

It also reduces the chance of him saying "no" as he has 3 offers so what other choices are there?

Even if you're still paying for some of the expenses out of pocket, you've most likely drastically reduced your cost of living by eliminating most of if not all of your mortgage, property taxes, and/or insurance.

I wanted a community pool to reduce my liability.

Does anyone have any experience using oil and gas tax deductions (Intangible Drilling Costs: 100% tax deductible during the first year and tangible Drilling Costs: 100% tax deductible) to reduce tax liability against Roth conversions ?   

A good professional can often pay for themselves by increasing your rent rates, reducing vacancies, or protecting you from bad renters.