Obviously STRs and wedding venues are not really the same thing (but they could be), but I do loosely consider them related in the sense that it is a hybrid between a traditional real estate investment combined with a "hospitality" element in regards to management and operation.The obvious starting things to consider that I've thought of are finding a property manager who is good at and/or wants a hands on type of approach to managing the property, working with and having good relationships with wedding industry vendors in the area who you can trust, extra things to consider with insurance, taxes, and permits etc, extra maintenance and repairs costs factored into your cash flow analysis, and different types of marketing strategies.

.$500k combined appraised value....and you'll need a good equity position and strong cash flow.

The other strategy is to reload your ace by refinancing out the VA with a conv or fha option (whichever is better for you at the time) so you can rinse and repeat.Doing this alone can be effective because you can use a lot of other peoples money or OPM to build wealth for your future but, if you combine it with a BRRRR strategy it can be highly effective.If your VA loan is currently tied up then there are options to utilize conventional financing or FHA too with low down depending on your situation, otherwise a strategy similar to the above.In Clark county, WA you can actually cashflow still after doing a BRRRR which is good news because this is not true in many high cost areas of seattle where the rent to value is too low (5k rents per month / 1.5M house or .33% RV ratio).

If you can document the damage, they won't push back over whether it cost $400 or $600 to clean the dog crap out of the carpet because they know they're responsible.

Use a combination of the historical expenses and your property management company for the expense assumptions.

The area is becoming far too costly for them to live, so rather than moving them to a more affordable but remote area of CA, I was hoping to combine their relocation with purchasing and occupying my first rental. 

Just hard work combined with diligent saving and time.

Combine this with a mortgage and it's near impossible to get ahead.

This being NJ I don't really have a lot of leverage over the tenants either other than threatening them with a 10% rent hike, no NJ judge would allow eviction over stupid crap like this, or even unpaid penalties I might impose.Do I just suck it up?

Hawaii's population is very debt adverse so people are very fiscally conservative... that combined with the fact that the ohana comes in and helps if anyone falls behind.... means little to no foreclosures.In addition wholeselling is extra tough because Hawaii just has so much dumb money and international money chasing non cashflow deals that don't make sense.