And if you're living on the property, you'll be able to monitor what goes on.As far as the price you can get when you sell, well that's driven a lot by demand.

In short I said if a deal doesn't cashflow with a regular downpayment % such as 20-25, throwing more money into it won't make it a killer deal.

There are definitely others ways to finance and perhaps get better returns, however, as I mentioned, this is assuming you would be using a regular conventional loan with 25% down payment.All real estate investments are on a case by case basis, make sure you run your numbers well, you must perform your due diligence on whatever investment property you purchase, as these numbers may apply to some but not all properties in Newark, NJ - Essex County. 

My vacation rental is 30 minutes away and somewhat remote so it's not checked regularly in the winter.

When receiving cash, always provide a receipt and make sure it itemizes what the cash covers.Unless there is a legitimate reason to provide the tenant with a receipt, we don't.We've only had one tenant request regular receipts and it was to show her case manager, related to monetary support she was receiving.

If, after the property evaluations come back, the deal meets our criteria we would extend a loan offer, and at that time the regular types of loan costs come into play.

Do those numbers get transferred to a schedule E or am I actually paying regular old 1099 self employment tax?? 

The lingo in the US is different then in NZ, so sometime asking questions helps to clarify few points.We also don't have large, cash flowing multifamily building so yes, im getting myself educated on regular bases. and will probably continue my education forever. 

And we have a VA appraiser here that kills deals on the regular and in his mind he is helping veterans from overpaying.

Flexibility on purpose what you can use funds for.Other options are to save in regular mutual funds contributing on a monthly basis- taking advantage if dollar- cost averaging..You may want to talk to one of the financial planners.