However I'm thinking if I ever hit the windfall on something like this, their pockets are probably way deeper than mine and I'm not going to want to spend the money to fight it.

Full Occupancy: The property achieved full occupancy within three weeks of listing, with strong tenant demand.High Cash Flow: The property generates $5,570/month in gross revenue and approximately $4,690/month in net profit after operating costs.Effective Use of 1031 Exchange: $300k of the total $420k investment was offset by the 1031 exchange, minimizing out-of-pocket expenses.Long-Term Stability: Designed for durability and versatility, the property is expected to cash flow for decadesLessons learned?

you're "out of pocket" those costs, plus maybe a month of vacancy.my point - you're basically always out of pocket on a rental. sometimes the rent more than covers everything, other times it doesn't. 

A receipt is required if you make an out-of-pocket cash purchase for > $75....

Quote from @Nathan Gesner: Quote from @Don Konipol: Consider the audience. 99% of BP visitors are small-time investors who will never face lawsuits from investors with deep pockets.

Our business plan actually includes rehabbing distressed properties and conducting off-market transactions with owners currently occupying distressed properties using equity to reduce the out of pocket costs for the seller/buyer and to simplify the process.

They are generous on the values so sometime my actual cash out of pocket is less than 15%, for example, I pay 102K for a house that appraises for 108K, the extra 6K they count towards my down payment so I get a mortgage for 91,800 because that's 85% of 108K and I write a check for about 10K.

I used Stacey Lancaster (she's pretty active on Bigger Pockets) and she was fantastic. 10/10 would recommend to a friend.

Transitioning to a Second Property with Low Money DownIf a second FHA loan is not an option, here are alternative strategies to minimize your out-of-pocket expenses:Conventional Loan with 5% Down: Once you’ve added equity to your current property, consider refinancing into a conventional loan to free up your FHA eligibility.

In most cases I have to pay out of pocket every month because rents are not high enough or the property is too expensive.