One or two little mistakes in your underwriting, a miss on the walkthrough, and you will blow right through your profit and come out in negative. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Tenant took photos and videos but nothing detailed - a single shot or two of a room from the entrance, so is saying fridge was fine, normal wear etc Next - If we are being nice and deducting ‘portions’ of the charges and tenant continues to grind away, or this goes to court, do the compromise and smaller amounts offered negate the full amounts that could have been charged

No negative action however ridiculous was not stifled, instead it was declared the system need conform to facilitate there whims however ridiculous. 

But yes, for LTR you will be negative most likely.

Perhaps your rents are just higher, but I wouldn’t suggest getting into a negatively cash flowing property especially for your first one.

Teak REI is more about appreciation and value add versus cash flow which is primarily negative until the harvest period.Are teak plantations a good investment?  

I believe San Diego is a great RE market but the reality is it is very competitive and most purchases have negative initial cash flow.  

Will getting this second home loan right now, affect me negatively when I go apply for the construction loan in the next 1-6 months?

So, even a small negative like a $50 unpaid cell phone bill that goes to collections when you switch carriers tanks their score.