I just closed a $2M condo on Indian Shores and luckily they did it all last year, but it did cost each unit $50-100k in special assessment.

I agree with Adam that there's not enough information here to say who is at fault.If you are spending all your income on maintenance after three years, then I would say you are being cheated by the PM or you bought a real dump.Personally, I would suck it up and find an expensive, but reliable, contractor to visit the property with me and make an assessment of what needs to be done to fix the property and stop the bleeding.

Now the minimum standards your basement has to hit for it to be able to count as assessed sqft not estimated is a height of 7 ft, a point of egress (bilco doors) and a window usually in the rear, It's one of those things where if your going to go through the process of digging out a basement you might as well go for it and dig it deeper then 7 and closer to 8 ft so you actually stand out compared to the competition.Now the other side of this coin which I would suggest is if you're willing to spend 40-50k on a basement dig, consider adding a 3rd story addition if your a 2 story (think master suite, walk in closet, master bath) or an addition off the back and add a roof deck if your a 3 story (either master suite or just additional bedroom).

This results in me often driving to the property to assess the problem myself and paying a premium to get the work done right. 

Risks such as regulatory, legal, financial, tax, and integration must be assessed and managed to proceed with a planned deal.

I've been doing this way longer than you have and I can guarantee that my first assessment is exactly what is happening.

If you're the type of investor to leave lucrative vacation rental investment to luck, then this post is not for you..It is intended for those that are looking for a fool proof strategy and tips to finding, assessing and buying an STR in the mid to near term. 1.

As an investor focused buyer's broker I spend the majority of my time helping buyer(s) assess properties both before and after their offer is accepted. 

When calculating cap, and other deal analysis criteria, none of them talks about how to assess the property in terms of its appreciation based on structural quality such as brick exterior versus vinyl.

The agent you spoke to should be ashamed of themselves for not asking you any questions and at least attempting to do a proper risk assessment.3.