Yes, you can ask them to be out by 10/29, but if they don't leave what will it cost you in terms of eviction costs, lost rent, damages, etc.2.

Personal readiness includes long-term plans, maturity, and market conditions.

Long-term trends appreciate over time.

But- since you are a newbie, in lay person's terms, the answer is yes...but slowly and over a very long time. 27.5 years, to be exact. 

I've heard that the down payment percentages for investment properties can be higher compared to primary residences.Specifically, I'm looking for insights on:The typical down payment percentages required by conventional lenders for investment properties.Any differences in requirements for single-family homes versus multi-unit properties.Experiences with different lenders and any recommendations for those offering favorable terms for investment properties.Any tips for negotiating better terms or finding lenders with more flexible down payment options.For context, this will be my second property, and I have a good credit score and a stable income.

Not including the principal reduction & tax benefits in your "flow".

Pete Beach have short-term rental restrictions.

I’d rather the potential for long term residual “passive income” as opposed to a one time profit.

The benefits to the investor are obvious. 

What's a fair amount, well that depends on what this is actually costing you in terms of actual expenses plus the time and hassle involved.