in summary all condo/HOA are bad investment except :- if they are located in prestigious location and/or neighborhood- they are relatively new so maintenance cost is low and predictable- they located in the market where DOM for condo is less than 10- they are located in the best school district- or they're located for resort zone/holiday zone.

my family runs a mom and pop shop at a ski shop in tahoe.

Definitely.Trying to go OOS for your first REI deal is a bit like trying to surf a monster 100 foot wave before you've learned to swim, or trying to ski a double black diamond for your very first run. 

Looking at single family or a duplex to start off the adventure, then sky's the limit after that.

Purchase price: $1,300,000 Cash invested: $16,000 Sale price: $2,000,000 With just 16k of our money, using creative finance, flipped this house in a ski-in location in about 50 days.

Proximity to Vail Mountain Resort.

@Aaron Washington Most of the resort style communities in and around Disney/Davenport are going to have a spa, they are all built that way.

I have 200k in liquid cash (yes this was self earned thru 5yrs of sacrifices and hard work 12-16hr days 7days a week with maybe a month in the summers as break to see family back home, but i dont want to do this forever) My dad and I want to be partners going into these deals. there is a new construction 4plex i am looking to build which will be 775k that i will put 25% down (half me half my dad) which will cash flow net 2k /mo if i rent it out LT (COC of 11% which isnt bad and apparently my agent who recently worked on a neighboring new build said the appraisal after its built is mid/high 800s, also my plan is after 2yrs to REFI at lower rate). i am considering to have 2 of the units as MTR for local nurses or construction crews which of course can increase profits much more.i also have a 3acre property that i am thinking to build small 2bd 1ba cabins and use as STR/MTR/LTR. but i am also wanting to do do STR as i love the concept and have watched Robuilt everyday learning from him. i am looking to buy land in a mountain/ski town (189k 10acres) and build a beautiful aframe and use as a STR. all these property ideas are close by to me so i will have a close look on them and will manage myself. i have just been consuming knowledge endlessly the last 3months in preparation for this decision.but as you can see my head is all over and im unsure what the correct first step will be. i have many goals and visions of what i want to do i just need some help making a correct first decision on those who are far more experienced than me in this real estate space so i use my capital in the most efficient way. i understand real estate is long game and i have no issues with that but i would like to at a minimum cashflow 100k a month by the time im 30. this is a big goal but i have 8yrs to do this. thank you for your help i look forward to the responses(side note: i am not considering house hacking as i live with my family, this will possibly be an option in the future)

Locate your home in a top resort and add really high quality theming that makes it pop online.

You also get the skiing traffic in the cold season (when it used to snow here).