And how can we align our approach to meet those expectations and improve our chances of securing financing?  

As long as you’re building with future hurricanes (wind and flood) in mind you can ensure that you’re prepared for future storms.  

Use caution while investing - don't expect things to go always right all the time. 

I'd be heavily focused on mitigating that future tax liabilty rather than directly supplementing that income.

@Nick Rutkowski no good deed goes unpunished by desperate people:(We try cash-for-keys (CFK) all the time, but tenants always think they're smarter than us.Most are so ignorant, they expect the funds BEFORE they move out.NEVER!

During the peak season you have to make your money when the slow season is so much less.I do have events where the prices are expected to be high due to supply and demand.I do see some of the dynamic pricing days as being rediculous and your going to miss out on the early bookers looking for a fair price.

From my experience you should expect a 10% to 15% of gross revenue for repairs/maintenance. 

Disclosure: Previous, current and future purchaser of Matt Scott's services.I have personally used Matt Scott and Incite Venture Capital to create my fixed income fund.

But be careful expecting to refinance.

@Joe Villeneuve @Theresa Harris, thanks a lot for taking the time and provide some info/ideas/suggestionsTo give you some color for these properties, there is a 15 years-plan that my wife and I are planning to have arround 5 to 7 properties in the same $$$ range (-+ $200K) that we can rent them around $1600-$1800I believe after 10 yrs, I am expecting to a better cash flow considering some loans will be paid in full, but maybe the next properties will have as you suggest 30 year-loan.