I just don’t think I would be comfortable at all with what my mortgage payments would be here on MAUI if I were to buy.

I find it usually takes three or four successful deals, or about 3 to 4 years investing with me, for an investor to become very comfortable.

Personal decision and comfort level question really.

Both wash up great and the comforters hang awesome on the beds.

They'll be most comfortable with lending at a lower loan amount since they'll have a better grasp/handle on the market.

You should choose one that makes you feel comfortable. 

Different states have different needs for contracts, and you want your title company to be comfortable with what's in your contract. 

@Travon Allender  As mentioned, if a bank will lend on a property in need of rehabbing, they will typically be a less costly resource (but not all banks are comfortable lending on non-cash flowing assets).

Although it’s 10 bedrooms now it could, with a little effort be turned into a very comfortable 4 bedroom 4 bath house.

And the replacement property must also be purchased with the intent of holding for productive use.Most folks feel comfortable with anything more than a year but there could always be situations where a hold period of less than (or more than) a year are needed to demonstrate your intent.On the plus side for you would be1. it appears you frequently hold property (the 2010 purchase) for longer term.  2.