I plan to move forward repainting the entire interior.

Both told me that their department doesn't do environmental studies on properties, and suggested to talk to the Planning & Zoning / Developmental Service.

If the numbers you’re hearing were from a property manager and you’re planning to do it yourself you will do much better than what you heard it was doing in the past :)

Our goal in investing is long term benefits (we would like to plan for retirement and helping our kids get started as adults), also plan to gain passive income, maybe gain one property every other year or so. 

But while the plan was always to house hack, I didn't spend enough time looking at what would make the best rental.

When I underwrite my deals, I plan on 5 years without a refi. 

My wife and I are both W2 and we are evaluating to buy a vacation home to enjoy it, but planning also on renting it as a STR while not being there.

The cost starts with  1.) plan cost (survey, civil engineer, site plan, architect, structural engineer, mechanical/electrical/plumbing (short for MEP) plans, etc.).

I planned to tell them that "I will waive the final 2 months of the lease but unfortunately I will have to keep your security deposit".

And is that where your also planning to invest?