If this was done prior to the reno, it's likely the majority of the cost can be written off as operating expenses under the De Minimis Safe Harbor.

Unfortunately we both live in such expensive, and possibly overheated, markets and are worried any purchase in either of these markets could be a terrible first investment!

I have 0 knowledge how real estate in Singapore is and weather if its a good idea to actually do real estate here as Singapore houses tends to be very expensive and there so many strict laws.

Some will say multi family is better because you have more income and proportionate expenses with higher cap rate.  

The addition income without addition expenses adds value to the property. 

I don't know that program, but many times the first meeting leads to an expensive coaching program for $25,000.  

So if a person invests wisely/conservatively in real estate (under 65% loan to value, stays away from excessively expensive properties that tend to default more, invest in the areas) perhaps the number drops to 20 or so.One suggestion: there is a fund called BroadMark Capital that invests in 100+ loans.

do you guys have any systems to keep your business expenses separate from the start for better tax planning if not forming a legal entity.

If you do not have equity in the property, the cost to borrow funds will be expensive.  

@Rita Koroll,As for HOAs, you need to consider them as an additional operating expense just like property tax.