.- An acceptable market entry range with factors such as the property price, down payment, and interest rate considered.- Do I enter immediately when I am financially ready, or should I wait until I’ve reached the projected savings allocated for this venture?

Cashflow would be better found in the Midwest where homes are still cheap and rents are OK. 

But, these properties are living, breathing and moving things that are all exactly the same, so you should just use your standard assumptions about payment and vacancy rates.

For example, investing on the south shore may offer affordable property prices, but it may also come with high crime rates and a less stable environment.

Then look at occupancy and nightly rate.

Your tenants will either pay market rates or move in with family. 

Break even cash flow or positive cash flow (on todays rates)Willing to do value add and development project I would do a house hack in your local market where you live.

@Liran AferganWe do medium-term rentals in our own rentals in Colorado Springs and Denver (and work with a lot of investors doing mid-term rentals), and the rental rates are more like 1.3-1.5x that of long-term rents.

If you are using an accounting software, it is impossible for the assets to not agree with the equity / liabilities.Did you factor in everything from the closing statement(such as pro-rated rent, closing costs, lender fees, etc)Did you use a PM company, if you did, did you factor in incorporating the PM Statements.Again, if you are using an accounting software, and factoring in all the transactions from your bank account / credit card, it should not be off.

Has the borrow rate historically been lower than the dividend rate?