Help rationalize this purchase -home w- 5 fig$ HOA / "buy in" nearly 50% home's price

[Tanya Solomon]

Hello, My Bigger Pocket peeps

Can you help a sister out here? I do not feel like I am my usual A-Game self lately and would appreciate other views, ideas, and or thoughts.  My mom recently (2 weeks ago today) died of cancer. We knew it was coming, but I was/am unprepared for how mentally disorientating it has been. "Normally," I am a pretty self-assured business person. I have made some good chunks of $ by being a hard worker that does a LOT of due diligence and trusting my gut. While I have been lucky in life (bc aren't we all to some degree? 1/3 the world's pop doesn't have access to potable drinking water), most of my "luck" was when opportunity met with my preparation.  I earned every $ I have. 

I am from NorCA and have bought and or sold about a dozen homes in the last decade. I can and have been creative and enjoy remodeling projects. Everything from gut remodels to light "fresh up'' where you paint and do easy things like light fixtures, drawer pulls, etc (isn't crazy how different a place can look with a few tweaks?) I NEVER overpay and EVERY purchase has to make sense financially, or I do not do it. I'm not the kind of person that would buy something just bc I really want it. 

Now I will say something that will probably sound diametrically opposed to my last statement. I am considering buying a home in an expensive "exclusive" golf country club community. The community I want to buy into (bc I think it is where we stand the best chance to be happy /WALKING DISTANCE TO SYNAGOGUE=Super important) is cheaper per sq ft but has a crazy MANDATORY "buy-in" of 150k AND HOA dues of around 45k a year....Are you still there? Yes, I am serious. Yes, it is a poop ton of $. Yes, it is 195K the 1st year- "right out the gate" Homes in this elite community range in price from the low 300s for a small duplex (no recent sales in the last 2 yrs) to 6 mil+ for a huge luxurious mansion. The avg home is around 850k-1.4mil plus the 150k buy-in and 45-50k a yr HOA. A good % of homes are bought with cash in my zip code.

I was in contract to purchase an REO home in this community that was over 1000 sq. bigger and in a more desirable location within the community = a better investment. But that deal fell through bc the Asset Management Co did not have their act together, told multiple lies, and wasted 2 months of my life and a few thousand of my $. *A big THX to all the ppl that helped me speculate what could be the hold-up on that transaction

****Here is the scenario and what I need help with. Say I have a 1 mil budget. Should I buy a cheap/small/least desirable area in the fancy golf course HOA home for 375K (2350 sq ft DUPLEX) and spend another 100-150k to remodel to not only make it nicer but max utility (500k+150k=650K all in), then buy a small investment home somewhere. OR wait until a bigger single-family home (one recently sold in about 2 weeks that was close to 3000 sq ft for 900k) with a better location comes on the market?

I HAVE 3 MONTHS B4 WE HAVE TO MOVE. 6k month rental =72 per yr (no security, no amenities) we have been in for almost a year is selling. I dislike the neighborhood, and they also want 1.6 for the 2400 sq ft home. The neighborhood the rental is in is a very low HOA but super high home price. It has a ghost town feel bc so many ppl snatched the homes up as vacation homes decades ago. Nobody sells unless they get crazy high $ or they have to sell.

My biggest issue, and what I want advice on, is how bad is it to buy the cheapest home in a super expensive area. There are 2 homes on the same street for sale. Both have not sold for months. bc they were grossly overpriced. Both are chasing the market down. The other one was beautifully remodeled (I'm guessing at least 150k remodel) and it is only 125k more. The remodel is the popular WHITE AND GRAY my nightmare CONTEMPORARY. I cant STAND this style!!! Im guessing that at this price range, ppl that can afford a 150k buy-in AND 45k HOA per yr do not want to live in a small duplex home. Also, it is hard to find comps for these homes bc there is only one street with about a dozen duplexes in the community.

Also, how do you make an offer on a home when there are no comps or if the comps are not really comps? 

. Thanks!!!