If you sell or transfer the property - that basis is re-evaluated at the time of the new sale  and would likely increase - making your taxes higher.  

Fair Return:An owner can also file a petition for a rent increase based onfair return.

A cost segregation study looks at a property you own to breakdown the various assets you purchased.The goal is to increase the depreciation expense by finding assets that have an asset life less than 27.5(residential) or 39 years(non-residential).Whether you should get a cost segregation study done is whether you will benefit from the study.Will you be able to use the added depreciation now or in the near future?

.- Getting tenants to agree to rent increases and turning in all the required paperwork to caseworker, then, you guessed it, chasing them to process it- Dealing with the tenant's "entitlement attitude" that they don't have to follow the terms of the lease, so they move in other individuals and/or get pets without permission.So, a good PMC will charge something more to manage a S8 tenant/property - either a higher percentage or a one-time or annual fee.

After I rehab it let’s say I put $30K in rehab work, on average how much would my property increase in value?

We do want to offer flexibility, our goal is to keep the tenants so if increasing only $25 a month the first year keeps them we are open to it. 

Do you think values in 39212 (SouthJackson) have increased since 2018?

@Neal Coppola As mentioned above, inventory has increased significantly for these lots, but with that being said, the overwhelming majority of those aren't listed anywhere close to what I would consider a reasonable price.

Investing in distant markets increases your risk and/or increases your costs. 

Everyday my respect for you Ben is increasing.