What have you learned to be the biggest determining factors of success when it comes to raising capital for a project?

The two biggest considerations are closing costs and hold time.

Whenever you are looking to end up with the biggest/most expensive house, be VERY conservative.

Before you spend a $1.00 on any investment, this is my BIGGEST piece of advise for you.

Biggest obstacle thus far is finding a good dependable/honest General Contractor.  

Here is the guide BP provides: https://www.biggerpockets.com/guidesThe biggest thing I have learned when it comes to tenant screening is to really look at tenants objectively.

However, the downside is that unless you are buying a distressed property or using creative finance, most banks are going to require you to put at least 15% down (but 20-25% is more common) for any investment property. 

The lake is ice cold in the spring so June to Oct is our time and we are usually full.The biggest negatives are the higher cost of insurance if you cover the beach area and dock.

The only downside is that you can only have one loan out like this at a time and the home must be owner occupied.

My BIGGEST concern is a dirty title.