partner with a RE attorney in your state, and get a PM company for the future

However, he is concerned about what might happen to the property in the future once I am gone.

You will have to make some estimations about future growth as any underwriter does. 

Or if they want a high interest rate, and your numbers will not work at that interest rate, or if they really want a crazy high price where it will be difficult to cash flow and refinance in the future.

Of course you can refi, but you wont be able to do a full cash our with rent covering your mortgage so you can keep rolling the funds to next project. 

Consider how you'll reinvest rental income, save for future down payments, and scale your real estate portfolio over time.Ultimately, the decision to invest in real estate or continue with your index fund investment depends on your individual circumstances, goals, and risk tolerance.

It would be beneficial for your future bookkeeper to have these expectations in mind where they reconcile the monthly statements and then just immediately send you a trial balance for approval. 

Ill explain my situation the best I can...Ive got a 100% remote corporate w2 Job making approximately 200k that offers a bit of flexibility since its mostly just project work.

Furthermore, by analyzing the last five years, we may deduce the present trend and future expansion possibilities.The pitfall of emotional connection, ah-hem.

Let me know how your project turns out.