Preparing a tax return with one long-term rental is not rocket science.

Quote from @Waruna Yapa: Quote from @Patrick Roberts: The competence and expertise of the lender absolutely matter, as do the terms of the product.  

I had never heard the term Proffers before  LOL.. 

The terms would be quite lucrative for the cash provider, they would be looking at a 30% return on their $$ in 2 years*

There may be requirements to cover the trash service depending on the town.My first commercial loan was 30% down, 20 year term (adjusting after the first 5 years). 

The only exception might be if you plan to and if your market supports short term rentals.

With that being said, if you're comfortable with a long term hold, San Diego and especially coastal, will always be attractive imo. 

The other thing that I would look at is private money too you can get it for cheaper and less pricy as they can make their own terms with their money.  

I will be furnishing one side for now and leasing to a mid term rental until i get a property management company that will work the property or get it leased out to students What was the outcome?

Or maybe a liquor store, which may seem innocent, but could bring in a different crowd.In terms of "when to sell," it's all about what you plan on doing with the money.