These areas tend to offer slightly more flexibility, and depending on the size of the property you’re looking for, you might find larger units than in Portland.Also, as Scott mentioned, increasing rents in Portland can be a slow process, especially with the 10% cap or 7% + CPI limits, whichever is lower.

It always tends to complicate the case.

Rates tend to be higher, since these aren't "conventional" loans that are going to be bought by Fannie or Freddie. 

Read these forums for awhile and you'll notice a trend among new investors buying out of state in crappy locations strictly for cash flow (they tend to lose money for a few years then sell the properties at a loss).

This is within my wheelhouse as construction loans are what I tend to focus on the most. 

A business or some estate planning attorneys may be able to assist you.CPAs tend to be best for consulting with the tax and numerical implications as to how it can affect your bottom line, and consulting as to the structure and right type of entity for you. 

There are definitely pros and cons to each so I figured I would just lay out a few benefits and personal thoughts: Small banks/brokerages:Pros:- Some regional knowledge of the market- Possibility of more creative lending guidelines with bank specific programs- Sometimes they have competitive rates for their areaCons: - weak balance sheet (more strict on some guidelines, no wiggle room, inability to be flexible or grant exceptions because they cannot afford to hold less than perfect loans)- Can't scale with clients to different markets- Usually limits exposure to individual investors (they don't want one investor to be too big of a portion of their balance sheet)- Lack of experience with multiple solutions (tend to have 2 or 3 loan products they sell and are too niche to provide tailored solutions)Large banks/brokerages:Pros:- Large compliance departments that understand individual market guidelines (typically each state has specific lending guidelines that augment the national baseline)- Ability to scale into multiple markets with same lender (licensed in many states)- Impossible for individual investors to "outgrow" a large bank's balance sheet (not concerned with one investor's concentration)- More lending solutions available for different scenarios- Often comparable or better rates given the game is volume basedCons:- Can be more difficult to get fast responses if the bank/brokerage does not have good follow up systems in place (or if the underwriting/processing staff gets overwhelmed)- Bad large banks can feel less like a relationship and more like a cog in a factory (less personal)Overall, I have worked from both and worked with both as a loan officer, branch manager, and as an investor/client myself. 

Small loans tend to be more expensive.

I have been looking at CRM's like Hubspot and Odoo and I tend to get a little overwhelmed because their tutorials all seemed to be geared towards those that have multiple people working on the CRM and all of this automation when all I want is a simple database.

In Florida, coastal areas tend to offer the best opportunities for STRs, especially given the saturation in the theme park areas of Central Florida but I'll let the full time operators chime in.