I'm on the Emerald Coast of FL (Destin - Fort Walton Beach) and I have noticed that there have been several investor developments, where an investor buys a property that also has some extra land and then adds tiny homes on the extra land to use for additional STR housing.

Hi @Ellen Feiss I agree with @Ty Coutts that you should start with informal, friendly, face-to-face conversations with the tenants to establish rapport, especially as you have some lead time here before next April.People don't like surprises or having to scramble, so if you are able to let them know your plans in advance, if they are reasonable people they should appreciate the extra lead time.This is especially true if their rents are currently very under market - they will have sticker shock when they look at what other units are renting for, and have to spend more time finding a new unit (if you'll be asking them to leave).If you have to move into one of the units yourself, I'm surprised you (or your lender) didn't make it a condition of the purchase and make the seller have the unit vacant for you.Sooner or later in rental real estate, you will have to establish a relationship with an eviction attorney.

At your price point there's a few areas that you could get into, but you'll need to keep in mind you'll need to have some extra funds for making any renovations you might need to maximize the property. 

This may be covered under the loan contingency, but I'd put it in as extra. 

Their address is XXXXX  53214b) Great Insurance Agents - NAME - EMAIL of insurance agent"For a tenant, you can let them know that renters insurance is very cheap and they can easily bundle it with their home and auto for only a few extra dollars month to protect their items if anything were to happen i.e. natural disaster .

All things equal, it seems this should perform better since it has the extra bedroom and it's only a couple blocks away from Main St.What do you think about the STR and MTR market in downtown Littleton compared to other submarkets in Denver metro?

This home has little cash flow and I was thinking i will hold long term but i am thinking if i should sell (will buy some Multifamily If i decided to sell with some extra cash) home this home or keep it.

The area and price range you mention  should go  very  quickly regardless of the time you list the property... when you sell - you can also ask the buyer to provide you with an extended closing date or lease back ( if you need some extra time before needing to move ) . 

Or then you look and by adding the cabinets, sink, and a separate entrance, you could get 150 a night but the extra rehab costs 20k to do, I think you have to look at taking less rent for putting in less money.To me, given where you seem to be new, I would go the cheap route to start. 

If you are going to take on the extra work required by an LLC, make sure you have a valid reason to do so.An LLC is useful for two things: anonymity and legal protection.