Can you 1031 a duplex (long term rental currently) or multiple duplexes to invest in a beach front property and use it as a short term rental?

Much better deal for you in the long run. 

He gives a discount on his hourly rate for rental property owners in hopes of making a long term relationship.

In many cases right now, I am pleased if the operator stops distributions in order to build up reserves and protect the asset - as long as they are sharing the reasons behind it.  

I am interested in exploring renting it out long or medium term.

Are you looking to hold on for long term appreciation while getting some cash flow or are you looking into other potential investment ideas?

Would prefer longer term loan 60 months or so but can do short term also ie 12-24 months.

Hello Ilya,Where are you looking at purchasing your 1st property.When converting a property from a single family to a multi family, you will need to check on the zoning requirements, depending on your location, not every location has zoning.As far as lending goes, it is far easier to finance a single family up to a quadplex, than financing 5 plus units, the DSCR Market for 5+ units is extremely low right now, and there are few if any lenders in that space.For financing 1-4 units, there are Millions of dollars chasing those loans, so you can easily obtain long term financing, at rates between 5-7%.Please reach out if you have a property identified, and I can help you with financing options.

I will show my loyalty to you, as long as I get it back. 

You should be able to get a 30Y DSCR loan under a 100k as long as the property value is 100k+.