We are currently working on how we are going to budget for these additional replacements.

My recommendation is to hang out with Alchemy of Money for a CPA and Engineered Tax Services for additional tax strategy. 

I have a very investor-friendly contractor (who offers pay-at-close in addition to conventional), and good clients who would be open to unconventional sales.

@Vikranth Biradar Here's an article with additional FAQs on cost segregation studies that you may find helpful.

The owner has done some questionable work with the kicker being an un-permitted unfinished addition that would either add 150 sqft or cost to remove/rebuild, still not sure how I want to approach this. 

In addition to what Michael said-if you do go ahead with purchasing it, write in the offer that they can not rent out the vacant half, deposit from the occupied side is transferred to you at closing along with prorated rent and get a copy of the lease that has been verified.

The professionals listed have additional training and ethic standards that set them a part, however it is important to conduct your own research and properly vet a few property managements before making your decision. 

This gives you the percentage return on your investment.Consider Additional Factors: Evaluate other factors such as potential appreciation, tax benefits (e.g., depreciation deductions), location desirability, market trends, and potential for future rental rate increases.By following these steps and considering all relevant factors, you can make informed decisions when analyzing the profitability of a rental property.

During this waiting period, consider house hacking, where you live in a multi-unit property and rent out the extra space for additional income.

They will receive and hold the cash proceeds from the sale and you will need to reinvest that into one or more replacement properties.