We're planning to start investing in real estate next spring once we reach our cash-saving goal.After some research and consideration, I believe the BRRRR strategy aligns well with our financial goals. 

The place could also survive on LT rent or seasonal rental, which is popular in this quaint village on the water for Summer and shoulder seasons.It's one of those two-story old 1890 brick buildings.

The HUD inspection the next day finds a water stain on the ceiling and fails the property.  

In fact two week ago I tried reasoning with a brainwashed Pace Morby follower in these forums who stated he would  happily complete a seller finance deal for more than FMV value, effectively putting him under water if he could acquire the property without using any of his money and the property cash flowed.

I know one option is to wade into the waters of private funding.

A little background though...last spring we finished a long renovation by mid-May and didn't get the house listed on AirBNB and Vrbo until early June, which was much later than we were planning, and we still filled the rest of the weekends for the summer.  

In the worst case, I may need to keep the property empty (while paying more than $4000 mortgage each month) until next Spring. 

The water is getting in from somewhere, and if left unaddressed, it could lead to bigger issues down the road.

The thing I would be worried about is that these two properties will consume your entire life, you will have to overspend on both, you will overdo it on both because of the attachment and will end up with properties that are worth way more to you (emotionally) than to the open market.Your area has starkly rising insurance costs because of fires and the property in Carlsbad being near the water now has strong flood risk so your insurance and holding costs are going to keep going up and up which may hold down the overall value.

As I am not a spring chicken with my age..there are always concerns about "What happens if I die?"...