Re-educating myself and ready to dip toes

My wife and I live in Central Maine, and are empty nesters now, and travel at least every other month but shoot for every month. Early retired (late fifties). We can afford decent “digs” and often spend $500+ per night. I’ve been shallow diving the concept of time shares for the past decade, and now I think it would make a good “tool” in our travel box, if nothing else. Here’s my back of the envelope thought process. PLEASE nudge me in the right direction and don’t be afraid to tell me where I’m way off!

We “staycation” 4-5 weeks mid coast Maine (Old Orchard Beach and my family’s Boothbay Harbor house that we’re lucky to get a couple weeks a year while it’s still standing!) Otherwise we do tend to end up visiting friends in St. Pete area and Key West. We love Florida, especially below the “coconut line” where we don’t get too many unexpected 45 degree weeks in winters. We also want to start traveling to Europe, Mexico, Central America. And definitely Aruba. TS may or may not be a useful tool in every travel instance, but I lay this all out to help you help me. My wife could be a travel agent. She’ spends an hour a day checking on all our booked hotel and airfare and rebooking when they go down. So we’re “cut out” for the complexities. In this regard I’m laying the foundation then once I assemble a “portfolio” I’ll turn it over to her!

1. First, I thought it might be good to have a cheap week in Maine (Samoset is supposedly the best TS system in Maine, though the one in Southwest Harbor, family owned, is supposed to great too. In fact they handle all the resales in house. THIS would serve two purposes: 1. Give us the choice of staycation OR trade, and gets us in “the door” so we can access deals via RCI (we’ll be members of one or both RCI/II)

2. Points strike me as a simpler, more versatile way … we REALLY love our home and find ourselves “ready to come home” after 4-5 days, so we often structure our trips for 5-6 days including travel days. Wyndham comes highly recommended from past forum inquiries but members cite steep learning curve.

3. What “limits” should I set or expect for fees? I’ve heard “try to keep it to .01 or less per RCI point?

4. Speaking of points…do all TS’s have an easy to find RCI/II point equivalent? (if not in listing)

5. I’ve read over and over that lockouts can be a great bargain, because when you split them up, you can use them as more points overall for trading? (i.e. 120,000 points for a 2BR LO, you “lock em out” and deposit them as 2 different units and you get 100K points for the bigger and 80K for the smaller? Just an example…but am I on the right track? Or sleep in the bigger half and always rent out the smaller?

6. Also read that one should buy TS’s in well established systems that are expanding. What’s an easy way to know this? I mean I know the “big guns” like Wyndham, Hyatt, Hilton, etc.

7. We like “nice” but we don’t want to be saddled with too much of a bill each year (i.e. we’d be ok with pretty nice for $700 MF per year vs I”ve died and gone to heaven for $2,500 MF) We do favor Hilton family for hotels, if that helps? I know they have a system, but if they’re super high end we’re happy opting for something four star vs five neighborhood if that makes sense.

Okay, I don’t want to write a book, so I’ll leave it at that! I suppose at this point I just need help narrowing down what to look for (points vs weeks, and what system?)