I have done extensive research and countless hours of book studying but I need hands on experience.           

Offer to pay for any that they collect for you - this will give you a lot of insight on your competitors.Once you feel like you know your audience and your competitors you'll be ready to create kick-*** mailers, that aren't the same as 10 other people and a total waste of your money.

It will take you, say ,1 hour to do your first offer, search etc. and once you have the template, next time you need to put an offer in, it will take you mins ;pGo to any training your broker have you do to polish your realtor side.For me it's all about collective learning.  

Their collection agency sent me a letter saying i should pay dues to current date but i dont think thats right considering the HOA have been renting it out since 2013.Can some of that rent money the HOA have been collecting minus the monthly assessment cover some of the liens from the 15k?

There is little chance they will drop them but you can ask for an extension and get 1 year to correct3.  

Nine of which are vacation rentals in which no one but I, handle all aspects for renting, collection of rents, reservations, contact after they arrive, etc.....

I would like the collective input and wisdom of you, forum members, to test and prompt my further planning and pre-empting as I plan to write the contracts and do the transaction.

I've seen videos and read lots of random things that have collectively piqued my interest in the real estate world.

I cannot recommend them based on their work but I did extensive research before I had 3 of the vendors do quotes.  

I would typically look at historical collections and then make an estimate for future income.